Skip to main content
SpringerLink
Log in
Book cover

Low Molecular Mass Gelator pp 167–218Cite as

Chirality Effects in Self-assembled Fibrillar Networks

  • Chapter
  • First Online:

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 256))

Abstract

Chirality seems to be intimately associated with the growth and stability of self-assembled fibrillar networks and with the most common macroscopic property of these networks, which is the thermoreversible gelation of the solvent. The presence and the relative configurations of stereogenic centers in the structure of a small molecule gelator are generally (but not always) observed to be critical to its ability to form gels. Symmetry considerations of chiral molecular packing provide thermodynamic and kinetic arguments that may explain why chirality favors fiber growth. Additionally, molecular chirality is sometimes expressed at a scale of nanometers or micrometers and gives rise to twisted or coiled fiber structures that are readily observable by microscopic techniques. These chiral fiber morphologies have already found some applications as templates for helical protein crystallization or for the growth of chiral inorganic replicas. The chiroptical properties of assembled chiral molecules, e.g., circular dichroism, allow monitoring of aggregation and may sometimes give insights into molecular packing. But determining chiral molecular arrangements in the fibers remains a challenge and requires the use of multiple techniques.

This is a preview of subscription content, log in via an institution.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

AFM:

Atomic force microscopy

CD:

Circular dichroism

DIC:

Differential interference contrast

HRSEM:

High-resolution scanning electron microscopy

NMR:

Nuclear magnetic resonance

SEM:

Scanning electron microscopy

STM:

Scanning tunneling microscopy

TEM:

Transmission electron microscopy

VCD:

Vibrational circular dichroism

WAXS:

Wide-angle X-ray scattering

References

  1. Fuhrhop J-H, Helfrich W (1993) Chem Rev 93:1565

    Article  CAS  Google Scholar 

  2. Schnur JM (1993) Science 262:1669

    Article  CAS  Google Scholar 

  3. Kunitake K (1992) Angew Chem Int Ed 31:709

    Article  Google Scholar 

  4. Spector MS, Selinger JV, Schnur JM (2003) Chiral molecular self-assembly. In: Green MM, Nolte RJM, Meijer EW, Denmark SE, Siegel J (eds) Materials chirality. Topics in stereochemistry, vol 24. Wiley, Hoboken, NJ

    Google Scholar 

  5. Trager O, Sowade S, Bottcher C, Fuhrhop J-H (1997) J Am Chem Soc 119:9120

    Article  Google Scholar 

  6. Terech P, Weiss RG (1997) Chem Rev 97:3133

    Article  CAS  Google Scholar 

  7. Estroff LA, Hamilton AD (2004) Chem Rev 104:1201

    Article  CAS  Google Scholar 

  8. Luo X, Li C, Liang Y (2000) Chem Commun 2091

    Google Scholar 

  9. van Esch J, De Feyter S, Kellog RM, De Shryver F, Feringa BL (1997) Chem Eur J 3:1238

    Article  Google Scholar 

  10. Tomioka K, Sumiyoshi T, Narui S, Nagaoka Y, Iida A, Miwa Y, Taga T, Nakano M, Handa T (2001) J Am Chem Soc 123:11817

    Article  CAS  Google Scholar 

  11. Schoobeek FS, van Esch J, Hulst R, Kellog RM, Feringa BL (2000) Chem Eur J 6:2633

    Article  Google Scholar 

  12. Hanabusa K, Koto C, Kimura M, Shirai H, Kakehi A (1997) Chem Lett 429

    Google Scholar 

  13. Kölbel M, Menger FM (2001) Chem Commun 275

    Google Scholar 

  14. Yasuda Y, Takebe Y, Fukumoto M, Inada H, Shirota Y (1996) Adv Mater 8:740

    Article  CAS  Google Scholar 

  15. Brotin T, Utermöhlen R, Fages F, Bouas-Laurent H, Desvergnes J-P (1991) Chem Commun 416

    Google Scholar 

  16. Babu P, Sangeetha NM, Vijaykumar P, Maitra U, Rissanen K, Raju AR (2003) Chem Eur J 9:1922

    Article  CAS  Google Scholar 

  17. Lu L, Weiss RG (1996) Chem Commun 2029

    Google Scholar 

  18. Terech P, Allegraud JJ, Garner CM (1998) Langmuir 14:3991

    Article  CAS  Google Scholar 

  19. Saikaigudin Y, Shikata T, Urakami H, Tamura A, Hirata HJ (1987) Electron Microsc 36:168

    Google Scholar 

  20. Zana R, Xia J (eds) (2004) Gemini surfactants. Marcel Dekker, New York

    Google Scholar 

  21. Yoza K, Amanokura N, Ono Y, Akao T, Shinmori H, Takeuchi M, Shinkai S, Reinhoudt DN (1999) Chem Eur J 5:2722

    Article  CAS  Google Scholar 

  22. Gronwald O, Shinkai S (2001) Chem Eur J 7:4329

    Article  CAS  Google Scholar 

  23. Boettcher C, Schade B, Fuhrhop J-H (2001) Langmuir 17:873

    Article  CAS  Google Scholar 

  24. Bhattacharya S, Ghanashyam Acharya SN, Raju AR (1996) Chem Commun 2101

    Google Scholar 

  25. Fuhrhop J-H, Bedurke T, Hahn A, Grund S, Gatzmann J, Riederer M (1994) Angew Chem Int Ed Engl 33:350

    Article  Google Scholar 

  26. Mamiya JI, Kanie K, Hiyama T, Ikeda T, Kato T (2002) Chem Commun 1870

    Google Scholar 

  27. Hanabusa K, Yamada M, Kimura M, Shirai H (1996) Angew Chem Int Ed Engl 35:1949

    Article  CAS  Google Scholar 

  28. Fuhrhop J-H, Schnieder P, Rosenberg J, Boekema E (1987) J Am Chem Soc 109:3387

    Article  CAS  Google Scholar 

  29. de Loos M, van Esch J, Kellog RM, Feringa BL (2001) Angew Chem Int Ed 40:613

    Article  Google Scholar 

  30. Jokić M, Makarević J, Žinić M (1995) J Chem Soc Chem Commun 1723

    Google Scholar 

  31. Becceril J, Escuder B, Miravet JF, Gavara R, Luis SV (2005) Eur J Org Chem 481

    Google Scholar 

  32. Fuhrhop J-H, Boettcher C (1990) J Am Chem Soc 112:1768

    Article  CAS  Google Scholar 

  33. Singh A, Burke TG, Calvert JM, Georger JH, Herendeen B, Price RR, Schoen PE, Yager P (1988) Chem Phys Lipids 47:135

    Article  CAS  Google Scholar 

  34. Spector MS, Selinger JV, Singh A, Rodriguez JM, Price RR, Schnur JM (1998) Langmuir 14:3493

    Article  CAS  Google Scholar 

  35. Gulik-Krzywicki T, Fouquey C, Lehn J-M (1993) Proc Natl Acad Sci USA 90:163

    Article  CAS  Google Scholar 

  36. Yamada N, Sasaki T, Murata H, Kunitake T (1989) Chem Lett 205

    Google Scholar 

  37. Terech P, Rodriguez V, Barnes JD, McKenna GB (1994) Langmuir 10:3406

    Article  CAS  Google Scholar 

  38. Makarević J, Jokić M, Raza Z, Štefanić Z, Kojić-Prodić B, Žinić M (2003) Chem Eur J 9:5567

    Article  CAS  Google Scholar 

  39. Watanabe Y, Miyasou T, Hayashi M (2004) Org Lett 6:1547

    Article  CAS  Google Scholar 

  40. Čaplar V, Žinić M, Pozzo J-L, Fages F, Mieden-Gundert G, Vögtle F (2004) Eur J Org Chem 4048

    Google Scholar 

  41. Oda R, Huc I, Candau SJ (1998) Angew Chem Int Ed 37:2689

    Article  CAS  Google Scholar 

  42. Oda R, Huc I, Candau SJ, MacKintosh FC (1999) Nature 399:566

    Article  CAS  Google Scholar 

  43. Jacques J, Collet A, Wilen SH (1994) Enantiomers, racemates and resolutions, 3rd edn. Krieger, Malabar, FL

    Google Scholar 

  44. Wallach O (1885) Liebigs Ann Chem 286:90

    Google Scholar 

  45. Pratt Brock C, Schweizer WB, Dunitz JD (1991) J Am Chem Soc 113:9811

    Article  Google Scholar 

  46. Kitaigorodskii AI (1961) Organic chemical crystallography. Consultants Bureau, New York, pp 65–112

    Google Scholar 

  47. Makarević J, Jokić M, Perić B, Tomišić V, Kojić-Prodić B, Žinić M (2001) Chem Eur J 7:3328

    Article  Google Scholar 

  48. Menger FM, Yamasaki Y, Catlin KK, Nishimi T (1995) Angew Chem Int Ed Engl 34:585

    Article  CAS  Google Scholar 

  49. Masuda M, Shimizu T (1996) Chem Commun 1057

    Google Scholar 

  50. Snijder CS, de Jong JC, Meetsma A, van Bolhuis F, Feringa BL (1995) Chem Eur J 1:549

    Article  Google Scholar 

  51. Kinbara K, Hashimoto Y, Sukegawa M, Nohira H, Saigo K (1996) J Am Chem Soc 118:3441

    Article  CAS  Google Scholar 

  52. Becceril J, Burguete MI, Escuder B, Galindo F, Gavara R, Miravet JF, Luis SV, Peris G (2004) Chem Eur J 10:3879

    Article  CAS  Google Scholar 

  53. Yager P, Schoen PE (1984) Mol Cryst Liq Cryst 106:371

    Article  CAS  Google Scholar 

  54. Georger JH, Singh A, Price RR, Schnur JM, Yager P, Schoen PE (1987) J Am Chem Soc 109:6175

    Article  Google Scholar 

  55. Yamada K, Ihara H, Ide T, Fukumoto T, Hirayama C (1984) Chem Lett 1713

    Google Scholar 

  56. Kulkarni VS, Boggs JM, Brown RE (1999) Biophys J 77:319

    Article  CAS  Google Scholar 

  57. Sommerdijk NAJM, Lambermon MHL, Feiters MC, Nolte RJM, Zwanenburg B (1997) Chem Commun 1423

    Google Scholar 

  58. Tachibana T, Kambara H (1965) J Am Chem Soc 87:3015

    Article  CAS  Google Scholar 

  59. Tachibana T, Kambara H (1969) Bull Chem Soc Jpn 42:3422

    Article  CAS  Google Scholar 

  60. Schnur JM, Ratna BR, Selinger JV, Singh A, Jyothi G, Easwaran KRK (1994) Science 264:945

    Article  CAS  Google Scholar 

  61. McCrea JF, Angerer S (1960) Biochim Biophys Acta 42:357

    Article  Google Scholar 

  62. Ramanathan N, Currie AL, Colvin JR (1960) Nature 190:779

    Article  Google Scholar 

  63. Nakashima N, Asakuma S, Kim J-M, Kunitake T (1984) Chem Lett 1709

    Google Scholar 

  64. Fuhrhop J-H, Schnieder P, Boekema E, Helfrich W (1988) J Am Chem Soc 110:2861

    Article  CAS  Google Scholar 

  65. Yanagawa H, Ogawa Y, Furuta H, Tsuno K (1989) J Am Chem Soc 111:4567

    Article  CAS  Google Scholar 

  66. Kunitake T, Yamada N (1986) Chem Commun 655

    Google Scholar 

  67. Selinger JV, Spector MS, Schnur JM (2001) J Phys Chem B 105:7158

    Article  CAS  Google Scholar 

  68. John G, Jung JH, Minamikawa H, Yoshida K, Shimizu T (2002) Chem Eur J 8:5494

    Article  CAS  Google Scholar 

  69. Jung JH, John G, Masuda M, Yoshida K, Shinkai S, Shimizu T (2001) Langmuir 17:7229

    Article  CAS  Google Scholar 

  70. Sommerdijk NAJM, Buynsters PJJA, Akdemir H, Geurts DG, Pistorius AMA, Feiters MC, Nolte RJM, Zwanenburg B (1998) Chem Eur J 4:127

    Article  CAS  Google Scholar 

  71. Fuhrhop J-H, Köning J (1994) Membranes and molecular assemblies: the synkinetic approach. Royal Society of Chemistry, Cambridge

    Google Scholar 

  72. Boettcher C, Stark H, van Heel M (1996) Ultramicroscopy 62:133

    Article  CAS  Google Scholar 

  73. Aggeli A, Nyrkova IA, Bell M, Harding R, Carrick L, Mcleish TCB, Semenov AN, Boden N (2001) Proc Natl Acad Sci USA 98:11857

    Article  CAS  Google Scholar 

  74. Fuhrhop J-H, Demoulin C, Böttcher C, Köning J, Siggel U (1992) J Am Chem Soc 114:4159

    Article  CAS  Google Scholar 

  75. Chiruvolu S, Warriner HE, Haranjo E, Idziak SHJ, Rädler JO, Plano RJ, Zasadzinski JA, Safinya CR (1994) Science 266:1222

    Article  CAS  Google Scholar 

  76. Imae T, Hayashi N, Matsumoto T, Tada T, Furusaka M (2002) J Colloid Interface Sci 225:285

    Article  Google Scholar 

  77. Engelkamp H, Middelbeek S, Nolte RJM (1999) Science 284:785

    Article  CAS  Google Scholar 

  78. Takafuji M, Ihara H, Hirayama C, Hachisako H, Yamada K (1995) Liq Cryst 18:97

    Article  CAS  Google Scholar 

  79. Lu L, Cocker TM, Bachman TE, Weiss RG (2000) Langmuir 16:20

    Article  CAS  Google Scholar 

  80. Wang R, Geiger C, Chen L, Swanson B, Whitten DG (2002) J Am Chem Soc 122:2399

    Article  CAS  Google Scholar 

  81. Lyon RP, Atkins WM (2001) J Am Chem Soc 123:4408

    Article  CAS  Google Scholar 

  82. Gronwald O, Shinkai S (2001) J Chem Soc Perkin Trans 2 1933

    Google Scholar 

  83. Lin Y-C, Kachar B, Weiss RG (1989) J Am Chem Soc 111:5542

    Article  CAS  Google Scholar 

  84. Hafkamp RJ, Feiters M, Nolte RJM (1999) J Org Chem 64:412

    Article  CAS  Google Scholar 

  85. Koumoto K, Yamashita T, Kimura T, Luboradzki T, Shinkai S (2001) Nanotechnology 12:25

    Article  CAS  Google Scholar 

  86. Thomas B, Safinya CR, Plano RJ, Clark NA (1995) Science 267:1635

    Article  CAS  Google Scholar 

  87. Murata K, Aoki M, Suzuki T, Harada T, Kawabata H, Komori T, Ohseto F, Ueda K, Shinkai S (1994) J Am Chem Soc 116:6664

    Article  CAS  Google Scholar 

  88. Nakashima N, Asakuma S, Kunitake T (1985) J Am Chem Soc 107:509

    Article  CAS  Google Scholar 

  89. Svenson S, Messersmith PB (1999) Langmuir 15:4464

    Article  CAS  Google Scholar 

  90. Hanabusa K, Maesaka Y, Kimura M, Shirai H (1999) Tetrahedron Lett 40:2385

    Article  CAS  Google Scholar 

  91. Becerril J, Burguete MI, Escuder B, Luis SV, Miravet JF, Querl M (2002) Chem Commun 738

    Google Scholar 

  92. Shimizu T, Masuda M (1997) J Am Chem Soc 119:2812

    Article  CAS  Google Scholar 

  93. Nakazawa I, Masuda M, Okada Y, Hanada T, Yase K, Asai M, Shimizu T (1999) Langmuir 15:4757

    Article  CAS  Google Scholar 

  94. Schnieder J, Messerschmidt C, Schulz A, Gnade M, Schade B, Luger P, Bombicz P, Hubert V, Fuhrhop J-H (2002) Langmuir 16:8575

    Article  CAS  Google Scholar 

  95. Tachibana T, Kayama S, Takeno H (1972) Bull Chem Soc Jpn 45:415

    Article  CAS  Google Scholar 

  96. Shimizu T, Hato M (1993) Biochim Biophys Acta 1147:50

    Article  CAS  Google Scholar 

  97. Hafkamp RJ, Kokke BPA, Danke IM, Geurts HPM, Rowan AE, Feiters M, Nolte RJM (1997) Chem Commun 545

    Google Scholar 

  98. Thomas BN, Corcoran RC, Cotant CL, Lindemann CM, Kirsch JE, Persichini PJ (1998) J Am Chem Soc 120:12178

    Article  CAS  Google Scholar 

  99. Thomas BN, Lindemann CM, Clark NA (1999) Phys Rev E 59:3040

    Article  CAS  Google Scholar 

  100. Thomas BN, Lindemann CM, Corcoran RC, Cotant CL, Kirsch JE, Persichini PJ (2002) J Am Chem Soc 124:1227

    Article  CAS  Google Scholar 

  101. Zastavker YV, Asherie N, Lomakin A, Pande J, Donovan JM, Schnur JM, Benedek GB (1999) Proc Natl Acad Sci USA 96:7883

    Article  CAS  Google Scholar 

  102. Pakhomov S, Hammer RP, Mishra BK, Thomas BN (2003) Proc Natl Acad Sci USA 100:3040

    Article  Google Scholar 

  103. Yang W, Chai X, Chi L, Liu X, Cao Y, Lu R, Jiang Y, Tang X, Fuchs H, Li T (1999) Chem Eur J 5:1144

    Article  CAS  Google Scholar 

  104. von Berlepsch H, Kirstein S, Böttcher C (2003) J Phys Chem B 107:9646

    Article  CAS  Google Scholar 

  105. von Berlepsch H, Böttcher C, Ouart A, Regenbrecht M, Akari S, Keiderling U, Schnablegger H, Dähne S, Kirstein S (2000) Langmuir 16:5908

    Article  CAS  Google Scholar 

  106. Giuleri F, Krafft M-P, Riess JG (1994) Angew Chem Int Ed Engl 33:1514

    Article  Google Scholar 

  107. Giuleri F, Guillod F, Greiner J, Krafft M-P, Riess JG (1995) Chem Eur J 2:1335

    Article  Google Scholar 

  108. Matsui H, Pan S, Gologan B, Jonas SH (2000) J Phys Chem B 104:9576

    Article  CAS  Google Scholar 

  109. Lindsell WE, Preston PN, Seddon JM, Rosair GM, Woodman TA (2000) Chem Mater 12:1572

    Article  CAS  Google Scholar 

  110. Shimizu T, Iwaura R, Masuda M, Hanada T, Yase K (2001) J Am Chem Soc 123:5947

    Article  CAS  Google Scholar 

  111. Lvov YM, Price RR, Selinger JV, Singh A, Spector MS, Schnur JM (2000) Langmuir 16:5932

    Article  CAS  Google Scholar 

  112. Berthier D, Buffeteau T, Léger J-M, Oda R, Huc I (2002) J Am Chem Soc 124:13486

    Article  CAS  Google Scholar 

  113. Selinger JV, MacKintosh FC, Schnur JM (1996) Phys Rev E 53:3804

    Article  CAS  Google Scholar 

  114. Imae T, Takahashi Y, Muramatsu H (1992) J Am Chem Soc 114:3414

    Article  CAS  Google Scholar 

  115. Tachibana T, Mori T, Hori K (1980) Bull Chem Soc Jpn 53:1714

    Article  CAS  Google Scholar 

  116. Shirakawa M, Kawano S, Fujita N, Sada K, Shinkai S (2003) J Org Chem 68:5037

    Article  CAS  Google Scholar 

  117. Svenson S, Köning J, Fuhrhop J-H (1994) J Phys Chem 98:1022

    Article  CAS  Google Scholar 

  118. König J, Boettcher C, Winkler H, Zeitler E, Talmon Y, Fuhrhop J-H (1993) J Am Chem Soc 115:693

    Article  Google Scholar 

  119. van Esch J, Schoonbeek F, de Loos M, Kooijman HL, Spek A, Kellog RM, Feringa BL (1999) Chem Eur J 5:937

    Article  Google Scholar 

  120. Estroff LA, Hamilton AD (2000) Angew Chem Int Ed 39:3447

    Article  CAS  Google Scholar 

  121. Wang G, Hamilton AD (2003) Chem Commun 310

    Google Scholar 

  122. Ihara H, Yamagishi M, Takafuji M, Hachisato H, Hirayama C, Yamada K (1990) Nippon Kagaku Kaishi 1047

    Google Scholar 

  123. Nakashima T, Kimizuka N (2002) Adv Mater 14:1113

    Article  CAS  Google Scholar 

  124. Sagawa T, Fukugawa S, Yamada T, Ihara H (2002) Langmuir 18:2002

    Article  CAS  Google Scholar 

  125. Yun YJ, Park SM, Kim BH (2003) Chem Commun 254

    Google Scholar 

  126. Itojima Y, Ogawa Y, Tsuno K, Handa N, Yanagawa H (1992) Biochemistry 31:4757

    Article  CAS  Google Scholar 

  127. Abdallah DJ, Sirchio SA, Weiss RG (2000) Langmuir 16:7558

    Article  CAS  Google Scholar 

  128. Estroff LA, Leiserowits L, Addadi L, Weiner S, Hamilton AD (2003) Adv Mater 15:39

    Article  Google Scholar 

  129. Svenson S, Kirste B, Fuhrhop J-H (1994) J Am Chem Soc 116:11969

    Article  CAS  Google Scholar 

  130. Placin F, Desvergne J-P, Belin C, Buffeteau T, Desbat B, Ducasse L, Lassègues J-C (2003) Langmuir 19:4563

    Article  CAS  Google Scholar 

  131. Hoffmann H, Krämer U, Thurn H (1990) J Phys Chem 92:2027

    Article  Google Scholar 

  132. van der Schoot P, Cates ME (1994) J Chem Phys 101:5040

    Article  Google Scholar 

  133. Lachenmayer K, Oppermann W (2002) J Chem Phys 116:392

    Article  CAS  Google Scholar 

  134. Hong MK, Narayan O, Goldstein R, Shyamsunder E, Austin RH, Fisher DS, Hogan M (1992) Phys Rev Lett 68:1430

    Article  CAS  Google Scholar 

  135. Oizumi J, Kimura Y, Ito K, Hayakawa R (1996) J Chem Phys 104:9137

    Article  CAS  Google Scholar 

  136. Oda R, Lequeux F, Mendes E (1996) J Phys II (France) 6:1429

    CAS  Google Scholar 

  137. Prosser SR, Hunt SA, DiNatale JA, Vold RR (1996) J Am Chem Soc 118:269

    Article  CAS  Google Scholar 

  138. Katsaras J, Donaberger RL, Swainson IP, Tennant DC, Tun Z, Vold RR, Prosser RS (1997) Phys Rev Lett 78:899

    Article  CAS  Google Scholar 

  139. Rosenblatt C, Yager P, Schoen P (1987) Biophys J 52:295

    Article  CAS  Google Scholar 

  140. Terech P, de Geyer A, Struth B, Talmon Y (2002) Adv Mater 14:495

    Article  CAS  Google Scholar 

  141. Shklyarevskiy IO, Jonkheijm P, Christianen PCM, Schenning APHJ, Del Guerzo A, Desvergne J-P, Meijer EW, Maan JC (2005) Langmuir (in press)

    Google Scholar 

  142. Lescanne M, Colin A, Mondain-Monval O, Heuzé K, Fages F, Pozzo J-L (2002) Langmuir 18:7151

    Article  CAS  Google Scholar 

  143. Xing B, Yu C-W, Chow K-H, Ho P-L, Fu D, Xu B (2002) J Am Chem Soc 124:14846

    Article  CAS  Google Scholar 

  144. Mukhopadhyay S, Maitra U, Ira Krishnamoorthy G, Schmidt J, Talmon Y (2004) J Am Chem Soc 126:15905

    Article  CAS  Google Scholar 

  145. Glattli A, Daura X, Seebach D, van Gunsteren WF (2002) J Am Chem Soc 124:12972

    Article  CAS  Google Scholar 

  146. Craig DP, Power EA, Thirunamachandran T (1974) Chem Phys 27:149

    CAS  Google Scholar 

  147. Kawasaki T, Tokuhiro M, Kimizuka N, Kunitake T (2001) J Am Chem Soc 123:6792

    Article  CAS  Google Scholar 

  148. Maitra U, Mukhopadhyay S, Sarkar A, Rao P, Indi SS (2001) Angew Chem Int Ed 40:2281

    Article  CAS  Google Scholar 

  149. Spector MS, Singh A, Messersmith PB, Schnur JM (2001) Nano Lett 1:375

    Article  CAS  Google Scholar 

  150. Ihara H, Sakurai T, Yamada T, Hashimoto T, Takafuji M, Sagawa T, Hachisako H (2002) Langmuir 18:7120

    Article  CAS  Google Scholar 

  151. de Jong JJD, Lucas LN, Kellog RM, van Esch JH, Feringa BL (2004) Science 304:278

    Article  CAS  Google Scholar 

  152. Spector MS, Easwaran KRK, Jyothi GJ, Selinger JV, Singh A, Schnur JM (1996) Proc Natl Acad Sci USA 93:12943

    Article  CAS  Google Scholar 

  153. Green MM, Reidy MP, Johnson RJ, Darling G, O’Leary DJ, Willson G (1989) J Am Chem Soc 111:6452

    Article  Google Scholar 

  154. Iwaura R, Yoshida K, Masuda M, Oshini-Kameyama M, Yoshida M, Shimizu T (2003) Angew Chem Int Ed 42:1009

    Article  CAS  Google Scholar 

  155. Kobayashi H, Friggeri A, Koumoto K, Amaike M, Shinkai S, Reinhoudt DN (2002) Org Lett 4:1423

    Article  CAS  Google Scholar 

  156. Fuhrhop J-H, Svenson S, Boettcher C, Rossler E, Vieth H-M (1990) J Am Chem Soc 112:4307

    Article  CAS  Google Scholar 

  157. Menger FM, Caran KL (2000) J Am Chem Soc 122:11679

    Article  CAS  Google Scholar 

  158. Menger FM, Peresypkin AV (2003) J Am Chem Soc 125:5340

    Article  CAS  Google Scholar 

  159. Marini DM, Hwang W, Lauffenburger DA, Zhang S, Kamm RD (2002) Nano Lett 2:295

    Article  CAS  Google Scholar 

  160. Messerschmidt C, Svenson S, Stocker W, Fuhrhop J-H (2000) Langmuir 16:7445

    Article  CAS  Google Scholar 

  161. Moriyama M, Mizoshita N, Yokota T, Yokota T, Kishimoto K, Kato T (2003) Adv Mater 15:1335

    Article  CAS  Google Scholar 

  162. Ihara H, Shudo K, Hirayama C, Hachisako H, Yamada K (1996) Liq Cryst 20:807

    Article  CAS  Google Scholar 

  163. Sato I, Kadowaki K, Urabe H, Jung JH, Ono Y, Shinkai S, Soai K (2003) Tetrahedron Lett 44:721

    Article  CAS  Google Scholar 

  164. Jung JH, Ono Y, Hanabusa K, Shinkai S (2000) J Am Chem Soc 122:5008

    Article  CAS  Google Scholar 

  165. Ringler P, Müller W, Ringsdorf H, Brisson A (1997) Chem Eur J 3:620

    Article  CAS  Google Scholar 

  166. Wilson-Kubalek EM, Brown RE, Celia H, Milligan RA (1998) Proc Natl Acad Sci USA 95:8040

    Article  CAS  Google Scholar 

  167. Xia Y, Yang P, Sun Y, Wu Y, Mayers B, Gates B, Yin Y, Kim F, Yan H (2003) Adv Mater 15:353

    Article  CAS  Google Scholar 

  168. Van Bommel KJC, Friggeri A, Shinkai S (2003) Angew Chem Int Ed 42:980

    Article  Google Scholar 

  169. Mann S, Burkett SL, Davis SA, Fowler CE, Mendelson NH, Sims SD, Walsh D, Whilton NT (1997) Chem Mater 9:2300

    Article  CAS  Google Scholar 

  170. Jung JH, Shinkai S, Shimizu T (2003) Chem Rec 3:212

    Article  CAS  Google Scholar 

  171. Sone ED, Zubarev ER, Stupp SI (2002) Angew Chem Int Ed 41:1706

    Article  Google Scholar 

  172. Kobayashi S, Hamasaki N, Suzuki M, Kimura M, Shirai H, Hanabusa K (2002) J Am Chem Soc 124:6550

    Article  CAS  Google Scholar 

  173. Schnur JM, Price R, Schoen P, Yager P, Calvert JM, Georger J (1987) Thin Solid Films 152:181

    Article  CAS  Google Scholar 

  174. Burkett SL, Mann S (1996) Chem Commun 321

    Google Scholar 

  175. Goren M, Qi Z, Lennox RB (2000) Chem Mater 12:1222

    Article  CAS  Google Scholar 

  176. Seddon AM, Patel HM, Burkett SL, Mann S (2002) Angew Chem Int Ed 41:2988

    Article  CAS  Google Scholar 

  177. Ono Y, Nakashima K, Sano M, Kanekiyo Y, Inoue K, Hojo J, Shinkai S (1998) Chem Commun 1477

    Google Scholar 

  178. Jung JH, Lee S, Yoo JS, Yoshida K, Shimizu T, Shinkai S (2003) Chem Eur J 9:5307

    Article  CAS  Google Scholar 

  179. Moreau JEJ, Vellutini L, Wong Chi Man M, Bied C (2001) J Am Chem Soc 123:1509

    Article  CAS  Google Scholar 

  180. Jung JH, Yoshida K, Shimizu T (2002) Langmuir 18:8724

    Article  CAS  Google Scholar 

  181. Sugiyasu K, Tamaru S-I, Takeuchi M, Berthier D, Huc I, Oda R, Shinkai S (2002) Chem Commun 1212

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607, Pessac, France

    Aurélie Brizard, Reiko Oda & Ivan Huc

Authors
  1. Aurélie Brizard
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Reiko Oda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ivan Huc
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ivan Huc .

Rights and permissions

Reprints and permissions

Copyright information

© 2005 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Brizard, A., Oda, R., Huc, I. (2005). Chirality Effects in Self-assembled Fibrillar Networks. In: Low Molecular Mass Gelator. Topics in Current Chemistry, vol 256. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b107174

Download citation

Publish with us

Policies and ethics

Search

Navigation