Introduction to the Zeolite Structure-Directing Phenomenon by Organic Species: General Aspects

Chapter
Part of the Structure and Bonding book series (STRUCTURE, volume 175)

Abstract

During the last years, a tremendous progress has been achieved in the application of new zeolite materials in many different sectors through different pioneering innovations in the field of zeolite synthesis. At the very core of the production of these new zeolite materials lies the use of organic species as structure-directing agents (SDA), which has been recognized as the most important factor to determine the zeolite product rendered after the crystallization process. These organic species organize the inorganic zeolitic units and drive the crystallization pathway towards the production of particular zeolite framework types. This structure-direction phenomenon frequently works in combination with several other factors related to the chemical composition of the synthesis gels, mainly use of fluoride, concentration (H2O/T ratio), and presence of different heteroatoms, which are also relevant for the crystallization of particular zeolite materials. Several properties determine the structure-directing effect of these organic species, especially their molecular size and shape, hydrophobicity, rigidity vs flexibility, and hydrothermal stability. The properties of the zeolitic materials synthesized can be tuned up to a certain point through the use of rationally selected organic species with particular physico-chemical features as SDA. In this introductory chapter, we briefly review the history of the use of organic cations as SDAs, and give the fundaments of the different aspects related to this structure-direction phenomenon and factors affecting it, explaining the main properties of SDAs, providing some examples of recent uses and trends of organic SDAs, as well as the host–guest chemistry involved. In addition, we pay particular attention to the use of imidazolium-based organic cations as SDAs because of their current relevance in the synthesis of new zeolite materials.

Keywords

Host–guest Imidazolium Structure-directing agents Templates Zeolites 

Notes

Acknowledgements

Funding from the Spanish Ministry of Economy, Industry, and Competitiveness (through projects MAT2015-65767-P and MAT2015-71117-R) is acknowledged.

References

  1. 1.
    Cejka J, Corma A, Zones SI (2010) Zeolites and catalysis: synthesis reactions and applications. Wiley, WeinheimCrossRefGoogle Scholar
  2. 2.
    Davis ME (2002) Ordered porous materials for emerging applications. Nature 417:813–821CrossRefGoogle Scholar
  3. 3.
    Barrer RM (1948) Synthesis of a zeolitic mineral with chabazite-like sorptive properties. J Chem Soc 2:127–132CrossRefGoogle Scholar
  4. 4.
    Rabo JA, Schoonover MW (2001) Early discoveries in zeolite chemistry and catalysis at union carbide, and follow-up in industrial catalysis. Appl Catal A 222:261–275CrossRefGoogle Scholar
  5. 5.
    Breck DW, Eversole EG, Milton RM (1956) New synthetic crystalline zeolites. J Am Chem Soc 78:2338–2339CrossRefGoogle Scholar
  6. 6.
    Sherman JD (1999) Synthetic zeolites and other microporous oxide molecular sieves. Proc Natl Acad Sci 96:3471–3478CrossRefGoogle Scholar
  7. 7.
    Barrer RM, Denny PJ (1961) Hydrothermal chemistry of the silicates. Part IX.* Nitrogenous aluminosilicates. J Chem Soc:971–982Google Scholar
  8. 8.
    Kerr GT, Kokotailo GT (1961) Sodium zeolite ZK-4, a new synthetic crystalline aluminosilicate. J Am Chem Soc 83:4675–4675CrossRefGoogle Scholar
  9. 9.
    Kerr GT (1966) Chemistry of crystalline aluminosilicates. II. The synthesis and properties of zeolite ZK-4. Inorg Chem 5:1537–1539CrossRefGoogle Scholar
  10. 10.
    Wadlinger RL, Kerr GT, Rosinski EJ (1967) US Patent 3,308,069Google Scholar
  11. 11.
    Argauer RJ, Landolt GR (1972) US Patent 3,702,886Google Scholar
  12. 12.
    Kokotailo GT, Chu P, Lawton SL, et al. (1978) Synthesis and structure of synthetic zeolite ZSM-11. Nature 275:119–120CrossRefGoogle Scholar
  13. 13.
    Kerr GT (1963) Zeolite ZK-5: A new molecular sieve. Science 140:1412CrossRefGoogle Scholar
  14. 14.
    Wilson ST, Lok BM, Flanigen EM (1982) US Patent 4,310,440Google Scholar
  15. 15.
    Wilson ST, Lok BM, Messina CA, et al. (1982) Aluminophosphate molecular sieves: a new class of microporous crystalline inorganic solids. J Am Chem Soc 104:1146–1147CrossRefGoogle Scholar
  16. 16.
    Lok BM, Cannan TR, Messina CA (1983) The role of organic molecules in molecular sieve synthesis. Zeolites 3:282–291CrossRefGoogle Scholar
  17. 17.
    Kundy CS, Cox PA (2005) The hydrothermal synthesis of zeolites: precursors, intermediates and reaction mechanism. Microporous Mesoporous Mater 82:1–78CrossRefGoogle Scholar
  18. 18.
    Gies H, Marler M (1992) The structure-controlling role of organic templates for the synthesis of porosils in the system SiO2/template/H2O. Zeolites 12:42–49CrossRefGoogle Scholar
  19. 19.
    Moliner M, Rey F, Corma A (2013) Towards the rational design of efficient organic structure-directing agents for zeolite synthesis. Angew Chem Int Ed 52:13880–13889CrossRefGoogle Scholar
  20. 20.
    Burton AW, Zones SI (2007) Organic molecules in zeolite synthesis: their preparation and structure-directing effects. Stud Surf Sci Catal 168:137–179CrossRefGoogle Scholar
  21. 21.
    Nakagawa Y (1994) US Patent 5,281,407Google Scholar
  22. 22.
    Xie D, McCusker LB, Barlocher C, et al. (2013) SSZ-52, a zeolite with an 18-layer aluminosilicate framework structure related to that of the DeNOx catalyst Cu-SSZ-13. J Am Chem Soc 135:10519–10524CrossRefGoogle Scholar
  23. 23.
    Elomari S (2003) US Patent 6,616,911Google Scholar
  24. 24.
    Lew CM, Davis TM, Elomari S (2016) Synthesis of new molecular sieves using novel structure-directing agents (Chapter 2). In: Mintova S (ed) Verified syntheses of zeolitic materials, 3rd revised edition. XRD Patterns: N. Barrier. Published on behalf of the Synthesis Commission of the International Zeolite Association 2016, pp 29–35. ISBN: 978-0-692-68539-6Google Scholar
  25. 25.
    Moliner M, Rey F, Corma A (2016) Synthesis design of new molecular sieves (Chapter 3). In: Mintova S (ed) Verified syntheses of zeolitic materials, 3rd revised edition. XRD Patterns: N. Barrier. Published on behalf of the the Synthesis Commission of the International Zeolite Association 2016, pp 36–41. ISBN: 978-0-692-68539-6Google Scholar
  26. 26.
    Pérez-Pariente J, Gómez-Hortigüela L (2008) The role of templates in the synthesis of zeolites. In: Čejka J, Peréz-Pariente J, Roth WJ (eds) Zeolites: from model materials to industrial catalysts. Transworld Research Network, pp 33–62. ISBN: 978-81-7895-330-4Google Scholar
  27. 27.
    Davis ME, Lobo R (1992) Zeolite and molecular sieve synthesis. Chem Mater 4:756–768CrossRefGoogle Scholar
  28. 28.
    Ikuno T, Chaikittisilp W, Liu Z, et al. (2015) Structure-directing behaviors of tetraethylammonium cations toward zeolite beta revealed by the evolution of aluminosilicate species formed during the crystallization process. J Am Chem Soc 137:14533–14544CrossRefGoogle Scholar
  29. 29.
    Zones SI, Burton AW, Lee GS, et al. (2007) A study of piperidinium structure-directing agents in the synthesis of silica molecular sieves under fluoride-based conditions. J Am Chem Soc 129:9066–9079CrossRefGoogle Scholar
  30. 30.
    Jiang J, Yu J, Corma A (2010) Extra-large-pore zeolites: bridging the gap between micro and mesoporous structures. Angew Chem Int Ed 49:3120–3145CrossRefGoogle Scholar
  31. 31.
    Li J, Corma A, Yu J (2015) Synthesis of new zeolite structures. Chem Soc Rev 44:7112–7127CrossRefGoogle Scholar
  32. 32.
    Jiang J, Xu Y, Cheng P, et al. (2011) Investigation of extra-large pore zeolite synthesis by a high-throughput approach. Chem Mater 23:4709–4715CrossRefGoogle Scholar
  33. 33.
    Li Y, Yu J (2014) New stories of zeolite structures: their descriptions, determinations, predictions, and evaluations. Chem Rev 114:7268–7316CrossRefGoogle Scholar
  34. 34.
    Willhammar T, Sun J, Wan W, et al. (2012) Structure and catalytic properties of the most complex intergrown zeolite ITQ-39 determined by electron crystallography. Nat Chem 4:188–194CrossRefGoogle Scholar
  35. 35.
    Moliner M, González J, Portilla MT, et al. (2011) A new aluminosilicate molecular sieve with a system of pores between those of ZSM-5 and beta zeolite. J Am Chem Soc 133:9497–9505CrossRefGoogle Scholar
  36. 36.
    Moliner M, Willhammar T, Wan W, et al. (2012) Synthesis design and structure of a multipore zeolite with interconnected 12- and 10-MR channels. J Am Chem Soc 134:6473–6478CrossRefGoogle Scholar
  37. 37.
    Moliner M, Martínez C, Corma A (2015) Multipore zeolites: synthesis and catalytic applications. Angew Chem Int Ed 54:3560–3579CrossRefGoogle Scholar
  38. 38.
    Wang Z, Yu J, Xu R (2012) Needs and trends in rational synthesis of zeolitic materials. Chem Soc Rev 41:1729–1741CrossRefGoogle Scholar
  39. 39.
    Burton AW, Zones SI, Elomari S (2005) The chemistry of phase selectivity in the synthesis of high-silica zeolites. Curr Opin Colloid Interface Sci 10:211–219CrossRefGoogle Scholar
  40. 40.
    Boal BW, Zones SI, Davis ME (2015) Triptycene structure-directing agents in aluminophosphate synthesis. Microporous Mesoporous Mater 208:203–211CrossRefGoogle Scholar
  41. 41.
    Jackowski A, Zones SI, Hwang SJ, et al. (2009) Diquaternary ammonium compounds in zeolite synthesis: cyclic and polycyclic N-heterocycles connected by methylene chains. J Am Chem Soc 131:1092–1100CrossRefGoogle Scholar
  42. 42.
    Shvets O, Kasian N, Zukal A, et al. (2010) The role of template structure and synergism between inorganic and organic structure directing agents in the synthesis of UTL zeolite. Chem Mater 22:3482–3495CrossRefGoogle Scholar
  43. 43.
    Davis ME (2014) Zeolites from a materials chemistry perspective. Chem Mater 26:239–245CrossRefGoogle Scholar
  44. 44.
    Tsuji K, Beck LW, Davis ME (1999) Synthesis of 4,4’-trimethylenebis(1-benzyl-1-methylpiperidinium) diastereomers and their use as structure-directing agents in pure-silica molecular sieves syntheses. Microporous Mesoporous Mater 28:519–530CrossRefGoogle Scholar
  45. 45.
    Lee G, Nakagawa Y, Hwang S, et al. (2002) Organocations in zeolite synthesis: fused bicyclo [l.m.0] cations and the discovery of zeolite SSZ-48. J Am Chem Soc 124:7024–7034CrossRefGoogle Scholar
  46. 46.
    García R, Gómez-Hortigüela L, Sánchez F, et al. (2010) Diasteroselective structure directing effect of (1S,2S)-2-Hydroxymethyl-1-benzyl-1-methylpyrrolidinium in the synthesis of ZSM-12. Chem Mater 22:2276–2286CrossRefGoogle Scholar
  47. 47.
    Gallego EM, Portilla MT, Paris C (2017) “Ab initio” synthesis of zeolites for preestablished catalytic reactions. Science 355:1051–1054CrossRefGoogle Scholar
  48. 48.
    Burkett SL, Davis ME (1994) Mechanism of structure direction in the synthesis of Si-ZSM-5: an investigation by intermolecular 1H-29Si CP MAS NMR. J Phys Chem 98:4647–4653CrossRefGoogle Scholar
  49. 49.
    Burkett SL, Davis ME (1995) Mechanisms of structure direction in the synthesis of pure-silica zeolites. 1. Synthesis of TPA/Si-ZSM-5. Chem Mater 7:920–928CrossRefGoogle Scholar
  50. 50.
    Burkett SL, Davis ME (1995) Mechanism of structure direction in the synthesis of pure-silica zeolites. 2. Hydrophobic hydration and structural specificity. Chem Mater 7:1453–1463CrossRefGoogle Scholar
  51. 51.
    Kubota Y, Helmkamp MM, Zones SI, et al. (1996) Properties of organic cations that lead to the structure-direction of high-silica molecular sieves. Microporous Mater 6:213–229CrossRefGoogle Scholar
  52. 52.
    Jo C, Lee S, Cho SJ, et al. (2015) Synthesis of silicate zeolite analogues using organic sulfonium compounds as structure-directing agents. Angew Chem Int Ed 54:12805–12808CrossRefGoogle Scholar
  53. 53.
    Delprato F, Delmotte L, Guth JL, et al. (1990) Synthesis of new silica-rich cubic and hexagonal faujasites using crown-ether based supramolecules as templates. Zeolites 10:546–552CrossRefGoogle Scholar
  54. 54.
    Balkus KJ, Hargis CD, Kowalak S (1992) Synthesis of NaX zeolites with metallophthalocyanines. ACS Symp Ser 499:347–354CrossRefGoogle Scholar
  55. 55.
    Dorset DL, Kennedy GJ, Strohmaier KG, et al. (2006) P-derived organic cations as structure-directing agents: synthesis of a high-silica zeolite (ITQ-27) with a two-dimensional 12-ring channel system. J Am Chem Soc 128:8862–8867CrossRefGoogle Scholar
  56. 56.
    Wan Y, Zhao D (2007) On the controllable soft-templating approach to mesoporous silicates. Chem Rev 107:2821–2860CrossRefGoogle Scholar
  57. 57.
    Moteki T, Keoh SH, Okubo T (2014) Synthesis of zeolites using highly amphiphilic cations as structure-directing agents by hydrothermal treatment of a dense silicate gel. Chem Commun 50:1330–1333CrossRefGoogle Scholar
  58. 58.
    Cho M, Na K, Kim J, et al. (2009) Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts. Nature 461:246–249CrossRefGoogle Scholar
  59. 59.
    Kim W, Kim JC, Kim J, et al. (2013) External surface catalytic sites of surfactant-tailored nanomorphic zeolites for benzene isopropylation to cumene. ACS Catal 3:192–195CrossRefGoogle Scholar
  60. 60.
    Luo HY, Michaelis VK, Hodges S, et al. (2015) One-pot synthesis of MWW zeolite nanosheets using a rationally designed organic structure-directing agent. Chem Sci 6:6320–6324CrossRefGoogle Scholar
  61. 61.
    Seo Y, Lee S, Jo C, et al. (2013) Microporous aluminophosphate nanosheets and their nanomorphic zeolite analogues tailored by hierarchical structure-directing amines. J Am Chem Soc 135:8806–8809CrossRefGoogle Scholar
  62. 62.
    Corma A, Díaz-Cabañas MJ, Jorda JL, et al. (2008) A zeolitic structure (ITQ-34) with connected 9- and 10-ring channels obtained with phosphonium cations as structure directing agents. J Am Chem Soc 130:16482–16483CrossRefGoogle Scholar
  63. 63.
    Rey F, Simancas J (2017) Beyond nitrogen OSDAs. Struct Bond.  https://doi.org/10.1007/430_2017_13 (in this volume)
  64. 64.
    Villaescusa LA, Camblor MA (2016) Time evolution of an aluminogermanate zeolite synthesis: segregation of two closely similar phases with the same structure type. Chem Mater 28:3090–3098CrossRefGoogle Scholar
  65. 65.
    Caullet P, Guth JL, Hazm J, et al. (1991) Synthesis, characterization and crystal-structure of the new clathrasil phase octadecasil. Eur J Solid State Inorg Chem 28:345–361Google Scholar
  66. 66.
    Villaescusa LA, Barrett PA, Camblor MA (1998) Calcination of octadecasil: fluoride removal and symmetry of the pure SiO2 host. Chem Mater 10:3966–3973CrossRefGoogle Scholar
  67. 67.
    Caullet P, Paillaud JL, Mathieu Y, et al. (2007) Synthesis of zeolites in the presence of diquaternary alkylammonium ions as structure-directing agents. Oil Gas Sci Technol 62:819–825CrossRefGoogle Scholar
  68. 68.
    Lee SH, Shin CH, Yang DK, et al. (2004) Reinvestigation into the synthesis of zeolites using diquaternary alkylammonium ions (CH3)3N+(CH2)nN+(CH3)3 with n = 3–10 as structure-directing agents. Microporous Mesoporous Mater 68:97–104CrossRefGoogle Scholar
  69. 69.
    Rojas A, Gómez-Hortigüela L, Camblor MA (2013) Benzylimidazolium cations as zeolite structure-directing agents. Differences in performance brought about by a small change in size. Dalton Trans 42:2562–2571CrossRefGoogle Scholar
  70. 70.
    Parnham ER, Morris RE (2006) 1-Alkyl-3-methyl imidazolium bromide ionic liquids in the ionothermal synthesis of aluminium phosphate molecular sieves. Chem Mater 18:4882–4887CrossRefGoogle Scholar
  71. 71.
    Parnham ER, Drylie EA, Wheatley PS, et al. (2006) Ionothermal materials synthesis using unstable deep-eutectic solvents as template-delivery agents. Angew Chem 118:2084–5088CrossRefGoogle Scholar
  72. 72.
    Lee H, Zones SI, Davis ME (2003) A combustion-free methodology for synthesizing zeolites and zeolite-like materials. Nature 425:385–388CrossRefGoogle Scholar
  73. 73.
    Lee H, Zones SI, Davis ME (2005) Zeolite synthesis using degradable structure-directing agents and pore-filling agents. J Phys Chem B 109:2187–2191CrossRefGoogle Scholar
  74. 74.
    Lee H, Zones SI, Davis ME (2006) Synthesis of molecular sieves using ketal structure-directing agents and their degradation inside the pore space. Microporous Mesoporous Mater 88:266–274CrossRefGoogle Scholar
  75. 75.
    O’Brien MG, Beale AM, Catlow CRA, et al. (2006) Unique organic-inorganic interactions leading to a structure-directed microporous aluminophosphate crystallization as observed with in situ Raman spectroscopy. J Am Chem Soc 128:11744–11745CrossRefGoogle Scholar
  76. 76.
    Sánchez-Sánchez M, Sankar G, Gómez-Hortigüela L (2008) NMR evidence of different conformations of structure-directing cyclohexylamine in high-doped AlPO4-44 materials. Microporous Mesoporous Mater 114:485–494CrossRefGoogle Scholar
  77. 77.
    Bernardo-Maestro B, López-Arbeloa F, Pérez-Pariente J, et al. (2015) Supramolecular chemistry controlled by conformational space during structure-direction of nanoporous materials: self-assembly of ephedrine and pseudoephedrine. J Phys Chem C 119:28214–28225CrossRefGoogle Scholar
  78. 78.
    Takekiyo T, Yoshimura Y (2006) Raman spectroscopic study on the hydration structures of tetraethylammonium cation in water. J Phys Chem A 110:10829–10833CrossRefGoogle Scholar
  79. 79.
    Schmidt JE, Fu D, Deem MW, et al. (2016) Template–framework interactions in tetraethylammonium-directed zeolite synthesis. Angew Chem Int Ed 55:16044–16048CrossRefGoogle Scholar
  80. 80.
    Hong SB, Min HK, Shin CH, et al. (2007) Synthesis, crystal structure, characterization, and catalytic properties of TNU-9. J Am Chem Soc 129:10870–10885CrossRefGoogle Scholar
  81. 81.
    Gramm F, Baerlocher C, McCusker LB, et al. (2006) Complex zeolite structure solved by combining powder diffraction and electron microscopy. Nature 444:79–81CrossRefGoogle Scholar
  82. 82.
    Hong SB, Lear EG, Wright PA, et al. (2004) Synthesis, structure solution, characterization, and catalytic properties of TNU-10: a high-silica zeolite with the STI topology. J Am Chem Soc 126:5817–5826CrossRefGoogle Scholar
  83. 83.
    Bernardo-Maestro B, López-Arbeloa F, Pérez-Pariente J et al (2017) Comparison of the structure-directing effect of ephedrine and pseudoephedrine during crystallization of nanoporous aluminophosphates. Microporous Mesoporous Mater, published in web.  https://doi.org/10.1016/j.micromeso.2017.04.008 (in press)
  84. 84.
    Camblor MA, Hong SB (2011) Synthetic silicate zeolites: diverse materials accessible through geoinspiration. In: Bruce DW, O’Hare D, Walton IR (eds) Porous materials. Wiley, ChichesterGoogle Scholar
  85. 85.
    Flanigen EM, Patton RL (1978) US Patent 4,073,865Google Scholar
  86. 86.
    Guth JL, Kessler K, Higel JM, et al. (1989) Zeolite synthesis in the presence of fluoride ions. ACS Symp Ser 398:176–195CrossRefGoogle Scholar
  87. 87.
    Guth J, Kessler H, Caullet P et al (1993) F-: a multifunctional tool for microporous solids a) mineralizing, structure directing and templating effects in the synthesis. In: von Ballmoos R, Higgins J, Treacy M (eds) Proceedings of the 9th international zeolite conference, London, pp 215–222Google Scholar
  88. 88.
    Caullet P, Paillaud JL, Simon-Masseron A, et al. (2005) The fluoride route: a strategy to crystalline porous material. C R Chim 8:245–266CrossRefGoogle Scholar
  89. 89.
    Koller H, Lobo RF, Burkett SL, et al. (1995) SiO-···HOSi hydrogen bonds in as-synthesized high-silica zeolites. J Phys Chem 99:12588–12596CrossRefGoogle Scholar
  90. 90.
    Blasco T, Camblor MA, Corma A, et al. (1998) Direct synthesis and characterization of hydrophobic aluminum-free Ti-Beta zeolite. J Phys Chem 102:75–88CrossRefGoogle Scholar
  91. 91.
    Camblor MA, Corma A, Iborra S, et al. (1997) Beta zeolite as a catalyst for the preparation of alkyl glucoside surfactants: the role of crystal size and hydrophobicity. J Catal 172:76–84CrossRefGoogle Scholar
  92. 92.
    Eroshenko V, Regis RC, Soulard M, et al. (2001) Energetics: a new field of applications for hydrophobic zeolites. J Am Chem Soc 123:8129–8130CrossRefGoogle Scholar
  93. 93.
    Villaescusa LA, Camblor MA (2003) The fluoride route to new zeolites. Recent Res Dev Chem 1:93–141Google Scholar
  94. 94.
    Zicovich-Wilson CM, San-Román ML, Camblor MA, et al. (2007) Structure, vibrational analysis, and insights into host-guest interactions in as-synthesized pure silica ITQ-12 zeolite by periodic B3LYP calculations. J Am Chem Soc 129:11512–11523CrossRefGoogle Scholar
  95. 95.
    Zicovich-Wilson CM, Gándara F, Monge A, et al. (2010) In situ transformation of TON silica zeolite into the less dense ITW: structure-direction overcoming framework instability in the synthesis of SiO2 zeolites. J Am Chem Soc 132:3461–3471CrossRefGoogle Scholar
  96. 96.
    Camblor MA, Villaescusa LA, Díaz-Cabañas MJ (1999) Synthesis of all-silica and high-silica molecular sieves in fluoride. Top Catal 9:59–76CrossRefGoogle Scholar
  97. 97.
    Camblor MA, Barrett PA, Díaz-Cabañas MJ, et al. (2001) High silica zeolites with three-dimensional systems of large pore channels. Microporous Mesoporous Mater 48:11–22CrossRefGoogle Scholar
  98. 98.
    Zones SI, Darton RJ, Morris R, et al. (2005) Studies on the role of fluoride ion vs reaction concentration in zeolite synthesis. J Phys Chem B 109:652–661CrossRefGoogle Scholar
  99. 99.
    Burton AW, Lee GS, Zones SI (2006) Phase selectivity in the syntheses of cage-based zeolite structures: an investigation of thermodynamic interactions between zeolite hosts and structure directing agents by molecular modeling. Microporous Mesoporous Mater 90:129–144CrossRefGoogle Scholar
  100. 100.
    Zones SI, Hwang SJ, Elomari S, et al. (2005) The fluoride-based route to all-silica molecular sieves; a strategy for synthesis of new materials based upon close-packing of guest–host products. C R Chim 8:267–282CrossRefGoogle Scholar
  101. 101.
    Camblor MA, Díaz-Cabañas MJ, Cox PA, et al. (1999) A synthesis, MAS NMR, synchrotron X-ray powder diffraction, and computational study of zeolite SSZ-23. Chem Mater 11:2878–2885CrossRefGoogle Scholar
  102. 102.
    Lobo RF, Zones SI, Davis ME (1995) Structure-direction in zeolite synthesis. J Incl Phenom Macrocycl Chem 21:47–78Google Scholar
  103. 103.
    Catlow CRA, Coombes DS, Lewis D, et al. (1998) Computer modeling of nucleation, growth, and templating in hydrothermal synthesis. Chem Mater 10:3249–3265CrossRefGoogle Scholar
  104. 104.
    Jorge M, Auerbach SM, Monson PA (2005) Modeling spontaneous formation of precursor nanoparticles in clear-solution zeolite synthesis. J Am Chem Soc 127:14388–14400CrossRefGoogle Scholar
  105. 105.
    Piccione P, Yang S, Navrotsky A, et al. (2002) Thermodynamics of pure-silica molecular sieve synthesis. J Phys Chem B 106:3629–3638CrossRefGoogle Scholar
  106. 106.
    Piccione P, Woodfield B, Boerio-Goates J, et al. (2001) Entropy of pure-silica molecular sieves. J Phys Chem B 105(25):6025–6030CrossRefGoogle Scholar
  107. 107.
    Khan MN, Auerbach SM, Monson PA (2015) Lattice Monte Carlo simulations in search of zeolite analogues: effects of structure directing agents. J Phys Chem C 119:28046–28054CrossRefGoogle Scholar
  108. 108.
    Yu J, Xu R (2003) Rich structure chemistry in the aluminophosphate family. Acc Chem Res 36:481–490CrossRefGoogle Scholar
  109. 109.
    Lewis DW, Freeman CM, Catlow CRA (1995) Predicting the templating ability of organic additives for the synthesis of microporous materials. J Phys Chem 99:11194–11202CrossRefGoogle Scholar
  110. 110.
    Lewis DW, Willock DJ, Catlow CRA, et al. (1996) De novo design of structure-directing agents for the synthesis of microporous solids. Nature 382:604–606CrossRefGoogle Scholar
  111. 111.
    Schmidt JE, Deem MW, Davis ME (2014) Synthesis of a specified, silica molecular sieve using computationally predicted organic structure-directing agents. Angew Chem Int Ed 126:8512–8514CrossRefGoogle Scholar
  112. 112.
    Brunklaus G, Koller H, Zones SI (2016) Defect models of as-made high-silica zeolites: clusters of hydrogen-bonds and their interaction with the organic structure-directing agents determined from 1H double and triple quantum NMR spectroscopy. Angew Chem Int Ed 55:14459–14463CrossRefGoogle Scholar
  113. 113.
    Dib E, Grand J, Mintova S, et al. (2015) Structure-directing agent governs the location of silanol defects in zeolites. Chem Mater 27:7577–7579CrossRefGoogle Scholar
  114. 114.
    Gómez-Hortigüela L, Pinar AB, Corà F, et al. (2010) Dopant-siting selectivity in nanoporous catalysts: control of proton accessibility in zeolite catalysts through the rational use of templates. Chem Commun 46:2073–2075CrossRefGoogle Scholar
  115. 115.
    Román-Leshkov Y, Moliner M, Davis ME (2011) Impact of controlling the site distribution of Al atoms on catalytic properties in ferrierite-type zeolites. J Phys Chem C 115:1096–1102CrossRefGoogle Scholar
  116. 116.
    Yokoi T, Mochizuki H, Namba S, et al. (2015) Control of the Al distribution in the framework of ZSM-5 zeolite and its evaluation by solid-state NMR technique and catalytic properties. J Phys Chem C 119:15303–15315CrossRefGoogle Scholar
  117. 117.
    Gómez-Hortigüela L, Álvaro-Muñoz T, Bernardo-Maestro B, et al. (2015) Towards chiral distributions of dopants in microporous frameworks: helicoidal supramolecular arrangement of (1R,2S)-ephedrine and transfer of chirality. Phys Chem Chem Phys 17:348–357CrossRefGoogle Scholar
  118. 118.
    Lemishko T, Simancas J, Hernández-Rodríguez M, et al. (2016) An INS study of entrapped organic cations within the micropores of zeolite RTH. Phys Chem Chem Phys 18:17244–17252CrossRefGoogle Scholar
  119. 119.
    Gómez-Hortigüela L, Hamad S, Pinar AB, et al. (2009) Molecular insights into the self-aggregation of aromatic molecules in the synthesis of nanoporous aluminophosphates: a multilevel approach. J Am Chem Soc 131:16509–16524CrossRefGoogle Scholar
  120. 120.
    Wang Y, Yu J, Li Y, et al. (2003) Chirality transfer from guest chiral metal complexes to inorganic framework: the role of hydrogen bonding. Chem Eur J 9:5048–5055CrossRefGoogle Scholar
  121. 121.
    Gómez-Hortigüela L, Bernardo-Maestro B (2017) Chiral organic structure-directing agents. Struct Bond.  https://doi.org/10.1007/430_2017_9 (in this volume)
  122. 122.
    Behrens P, van de Goor G, Freyhardt CC (1995) Structure-determining C-H···O-Si hydrogen bonds in cobaltocenium fluoride nonasil. Angew Chem Int Ed 34:2680–2682CrossRefGoogle Scholar
  123. 123.
    Lee JK, Shin J, Ahn NH, et al. (2015) A family of molecular sieves containing framework-bound organic structure-directing agents. Angew Chem Int Ed 54:11097–11101CrossRefGoogle Scholar
  124. 124.
    Lee JK, Lee JH, Ahn NH, et al. (2016) Solid solution of a zeolite and a framework-bound OSDA-containing molecular sieve. Chem Sci 7:5805–5814CrossRefGoogle Scholar
  125. 125.
    Gómez-Hortigüela L, López-Arbeloa F, Corà F, et al. (2008) Supramolecular chemistry in the structure direction of microporous materials from aromatic structure-directing agents. J Am Chem Soc 130:13274–13284CrossRefGoogle Scholar
  126. 126.
    Corma A, Rey F, Rius J, et al. (2004) Supramolecular self-assembled molecules as organic directing agent for synthesis of zeolites. Nature 431:287–290CrossRefGoogle Scholar
  127. 127.
    Moliner M (2015) Design of zeolites with specific architectures using self-assembled aromatic organic structure-directing agents. Top Catal 25:502–512CrossRefGoogle Scholar
  128. 128.
    Paris C, Moliner M (2017) Role of supramolecular chemistry during templating phenomenon in zeolite synthesis. Struct Bond.  https://doi.org/10.1007/430_2017_11 (in this volume)
  129. 129.
    Corma A, Díaz-Cabañas MJ, Jordá JL, et al. (2006) High-throughput synthesis and catalytic properties of a molecular sieve with 18- and 10-member rings. Nature 443:842–845CrossRefGoogle Scholar
  130. 130.
    Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2084CrossRefGoogle Scholar
  131. 131.
    Arduengo AJ, Harlow RL, Kline M (1991) A stable crystalline carbene. J Am Chem Soc 113:361–363CrossRefGoogle Scholar
  132. 132.
    Brand SK, Schmidt JE, Deem MW, et al. (2017) Enantiomerically enriched, polycrystalline molecular sieves. Proc Natl Acad Sci U S A 114:5101–5106CrossRefGoogle Scholar
  133. 133.
    Zones SI (1989) Synthesis of pentasil zeolites from sodium silicate solutions in the presence of quaternary imidazole compounds. Zeolites 9:458–467CrossRefGoogle Scholar
  134. 134.
    Barrett PA, Boix T, Puche M, et al. (2003) ITQ-12: a new microporous silica polymorph potentially useful for light hydrocarbon separations. Chem Commun:2114–2115Google Scholar
  135. 135.
    Parnham ER, Morris RE (2006) The ionothermal synthesis of cobalt aluminophosphate zeolite frameworks. J Am Chem Soc 128:2204–2205CrossRefGoogle Scholar
  136. 136.
    Lorgouilloux Y, Dodin M, Paillaud JL, et al. (2009) IM-16: a new microporous germanosilicate with a novel framework topology containing D4R and MTW composite building units. J Solid State Chem 182:622–629CrossRefGoogle Scholar
  137. 137.
    Dodin M, Paillaud JL, Lorgouilloux Y, et al. (2010) A zeolitic material with a three-dimensional pore system formed by straight 12- and 10-ring channels synthesized with an imidazolium derivative as structure-directing agent. J Am Chem Soc 132:10221–10223CrossRefGoogle Scholar
  138. 138.
    Schmidt JE, Xie D, Rea T, et al. (2015) CIT-7, a crystalline, molecular sieve with pores bounded by 8 and 10-membered rings. Chem Sci 6:1728–1734CrossRefGoogle Scholar
  139. 139.
    Boal BW, Deem MW, Xie D, et al. (2016) Synthesis of germanosilicate molecular sieves from mono- and di-quaternary ammonium OSDAs constructed from benzyl imidazolium derivatives: stabilization of large micropore volumes including new molecular sieve CIT-13. Chem Mater 28:2158–2164CrossRefGoogle Scholar
  140. 140.
    Olson DH, Yang X, Camblor MA (2004) ITQ-12: a zeolite having temperature dependent adsorption selectivity and potential for propene separation. J Am Chem Soc 108:11044–11048Google Scholar
  141. 141.
    Rojas A, Martínez-Morales A, Zicovich-Wilson CM, Camblor MA (2012) Zeolite synthesis in fluoride media: structure direction toward ITW by small methylimidazolium cations. J Am Chem Soc 134:2255–2263CrossRefGoogle Scholar
  142. 142.
    Rojas A, San-Roman ML, Zicovich-Wilson CM, et al. (2013) Host−guest stabilization of a zeolite strained framework: in situ transformation of zeolite MTW into the less dense and more strained ITW. Chem Mater 25:729–738CrossRefGoogle Scholar
  143. 143.
    Rojas A, Camblor MA (2014) Structure-direction in the crystallization of ITW zeolites using 2-ethyl-1,3,4-trimethylimidazolium. Dalton Trans 43:10760–10766CrossRefGoogle Scholar
  144. 144.
    Rojas A, Camblor MA (2012) A pure silica chiral polymorph with helical pores. Angew Chem Int Ed 51:3854–3856CrossRefGoogle Scholar
  145. 145.
    Rojas A, Camblor MA (2014) HPM-2, the layered precursor to zeolite MTF. Chem Mater 26:1161–1169CrossRefGoogle Scholar
  146. 146.
    Rojas AE (2012) Dirección de estructuras en la síntesis de zeolitas usando cationes orgánicos imidazolios. PhD thesis, Universidad Autónoma de MadridGoogle Scholar
  147. 147.
    Cooper ER, Andrews CD, Wheatley PS, et al. (2004) Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues. Nature 430:1012–1016CrossRefGoogle Scholar
  148. 148.
    Parnham ER, Morris RE (2007) Ionothermal synthesis of zeolites, metal-organic frameworks, and inorganic-organic hybrids. Acc Chem Res 40:1005–1013CrossRefGoogle Scholar
  149. 149.
    Parnham ER (2006) Ionothermal synthesis. A new synthesis methodology using ionic liquids and eutectic mixtures as both solvent and template in zeotype synthesis. PhD thesis, University of St. AndrewsGoogle Scholar
  150. 150.
    Wagner P, Yoshikawa M, Lovallo M, et al. (1997) CIT-5: a high-silica zeolite with 14-ring pores. J. Chem. Soc, Chem. Commun 21:2179–2180CrossRefGoogle Scholar
  151. 151.
    Kang JH, Xie D, Zones SI, et al. (2016) Synthesis and characterization of CIT-13, a germanosilicate molecular sieve with extra-large pore openings. Chem Mater 28:6250–6259CrossRefGoogle Scholar
  152. 152.
    Tang L, Shi L, Bonneau C, et al. (2008) A zeolite family with chiral and achiral structures built from the same building layer. Nat Mater 7:381–385CrossRefGoogle Scholar
  153. 153.
    Kapko V, Dawson C, Treacy MMJ, et al. (2010) Flexibility of ideal zeolite frameworks. Phys Chem Chem Phys 12:8531–8541CrossRefGoogle Scholar
  154. 154.
    Sastre G, Corma A (2010) Predicting structural feasibility of silica and germania zeolites. J Phys Chem C 114:1667–1673CrossRefGoogle Scholar
  155. 155.
    Sartbaeva A, Wells SA, Treacy MMJ, et al. (2006) The flexibility window in zeolites. Nat Mater 5:962–965CrossRefGoogle Scholar
  156. 156.
    Medina ME, Platero-Prats AE, Snejko N, et al. (2011) Towards inorganic porous materials by design: looking for new architectures. Adv Mater 23:5283–5292CrossRefGoogle Scholar
  157. 157.
    Rojas A, Arteaga O, Kahr B, et al. (2013) Synthesis, structure and optical activity of HPM-1, a pure silica chiral zeolite. J Am Chem Soc 135:11975–11984CrossRefGoogle Scholar
  158. 158.
    Jo D, Hong SB, Camblor MA (2015) Monomolecular skeletal isomerization of 1-butene over selective zeolite catalysts. ACS Catal 5:2270–2274CrossRefGoogle Scholar
  159. 159.
    Pophale R, Daeyaert F, Deem MW (2013) Computational prediction of chemically synthesizable organic structure directing agents for zeolites. J Mater Chem A 1:6750–6760CrossRefGoogle Scholar
  160. 160.
    Schmidt JE, Deimund MA, Davis ME (2014) Facile preparation of aluminosilicate RTH across a wide composition range using a new organic structure-directing agent. Chem Mater 26:7099–7105CrossRefGoogle Scholar
  161. 161.
    Schmidt JE, Deimund ME, Xie D, et al. (2015) Synthesis of RTH-type zeolites using a diverse library of imidazolium cations. Chem Mater 27:3756–3762CrossRefGoogle Scholar
  162. 162.
    Jo D, Lim JB, Ryu T, et al. (2015) Unseeded hydroxide-mediated synthesis and CO2 adsorption properties of an aluminosilicate zeolite with the RTH topology. J Mater Chem A 3:19322–19329CrossRefGoogle Scholar
  163. 163.
    Schmidt JE, Xie D, Davis ME (2015) Synthesis of the RTH-type layer: the first small-pore, two dimensional layered zeolite precursor. Chem Sci 6:5955–5963CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2017

Authors and Affiliations

  1. 1.Instituto de Catálisis y Petroleoquímica (ICP-CSIC)MadridSpain
  2. 2.Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC)MadridSpain

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