Advertisement

Journal of Chemical Crystallography

, Volume 42, Issue 8, pp 809–815 | Cite as

Novel Salts of 2,4-Diaminoquinazoline: Searching for Materials for Second Harmonic Generation Based on a Promising Polarizable Cation

  • Michaela Fridrichová
  • Ivan Němec
  • Ivana Císařová
  • Nad’a Tesařová
  • Petr Němec
  • Aslı Karakaş
  • Nihal Kahraman
  • Mehmet Taşer
Original Paper

Abstract

The chloride and l-tartrate salts of the 2,4-diaminoquinazolinium(1+) were prepared and characterized by both X-ray diffraction and infrared spectroscopy. The potential of the 2,4-diaminoquinazolinium(1+) cation as a building block for materials for nonlinear optics was assessed using quantum mechanical computations. Both 2,4-diaminoquinazolinium(1+) chloride dihydrate (a = 7.2121(1) Å, b = 8.0105(2) Å, c = 18.6157(5) Å, β = 92.493(1)°, V = 1074.46(4) Å3, Z = 4, R = 0.0305 for 4605 observed reflections) and 2,4-diaminoquinazolinium(1+) l-tartrate dihydrate (a = 7.2899(2) Å, b = 11.9508(2) Å, c = 13.4183(3) Å, β = 92.375(2)°, V = 1168.00(5) Å3, Z = 2, R = 0.0367 for 4761 observed reflections) belong to the monoclinic space group P21. They are stable, non-hygroscopic, colorless and exhibit non-zero SHG efficiency for powdered samples.

Graphical Abstract

Two novel non-centrosymmetric salts of 2,4-diaminoquinazolinium(1+) were prepared and thoroughly characterized during the search for materials for the second harmonic generation.

Keywords

Nonlinear optics Second harmonic generation Hyperpolarizability Ab initio calculation Non-centrosymmetric assembly 2,4-diaminoquinazoline 

Notes

Acknowledgments

This work was supported by the Grant Agency of Charles University in Prague (Grant No. 58608), Czech Science Foundation (Grant No. 203/09/0878), long term Research Plan of the Ministry of Education of the Czech Republic (MSM-0021620857) and by the grant of the Selçuk University (Grant No. 08601258).

Supplementary material

10870_2012_318_MOESM1_ESM.doc (180 kb)
Supplementary material 1 (DOC 179 kb)

References

  1. 1.
    Park SK, Do JY, Ju JJ, Park S, Kim M-S, Lee M-H (2005) Mater Lett 59:2872CrossRefGoogle Scholar
  2. 2.
    Zyss J, Nicoud JF (1996) Curr Opin Solid State Mater Sci 1:354CrossRefGoogle Scholar
  3. 3.
    Ratajczak H, Baran J, Barycki J, Debrus S, May M, Pietraszko A, Ratajczak HM, Tramer A, Venturini J (2000) J Mol Struct 555:149CrossRefGoogle Scholar
  4. 4.
    Uesu Y, Yokota H, Kawado S, Kato N (2007) J Korean Phys Soc 51:804CrossRefGoogle Scholar
  5. 5.
    Provenzano PP, Eliceiri KW, Yan L, Ada-Nguema A, Conklin MW, Inman DR, Keely PJ (2008) Microsc Microanal 14:532CrossRefGoogle Scholar
  6. 6.
    Guru Row TN (1999) Coord Chem Rev 183:81CrossRefGoogle Scholar
  7. 7.
    Aakeröy CB, Seddon KR (1993) Chem Soc Rev 22:397CrossRefGoogle Scholar
  8. 8.
    Xue D, Zhang S (1996) J Phys Chem Solids 57:1321CrossRefGoogle Scholar
  9. 9.
    Xue D, Zhang S (1997) J Phys Chem A 101:5547CrossRefGoogle Scholar
  10. 10.
    Matulková I, Němec I, Císařová I, Němec P, Mička Z (2007) J Mol Struct 834:328CrossRefGoogle Scholar
  11. 11.
    Matulková I, Němec I, Císařová I, Němec P, Vaněk P (2010) J Mol Struct 966:23CrossRefGoogle Scholar
  12. 12.
    Zyss J, Pecaut J, Levy JP, Masse R (1993) Acta Crystallogr B 49:334CrossRefGoogle Scholar
  13. 13.
    Fridrichová M, Němec I, Císařová I, Němec P (2010) CrystEngComm 12:2054CrossRefGoogle Scholar
  14. 14.
    Lukeš V, Breza M, Végh D, Hrdlović P, Laurinc V (2003) Synth Met 138:399CrossRefGoogle Scholar
  15. 15.
    Marder SR, Beratan DN, Cheng LT (1991) Science 252:103CrossRefGoogle Scholar
  16. 16.
    Vopicka E, Lange NA (1935) J Am Chem Soc 57:1068CrossRefGoogle Scholar
  17. 17.
    Dener JM, Lease TG, Novack AR, Plunkett MJ, Hocker MD, Fantauzzi PP (2001) J Comb Chem 3:590CrossRefGoogle Scholar
  18. 18.
    Zerweck W, Kunze W (1943) I. G. Farbenindustrie Germany, application DE 737931 19430701Google Scholar
  19. 19.
    Krishnakumar V, Xavier RJ (2005) Chem Phys 312:227CrossRefGoogle Scholar
  20. 20.
    Ommeh S, Nduati E, Mberu E, Kokwaro G, Marsh K, Rosowsky A, Nzila A (2004) Antimicrob Agents Ch 48:3711CrossRefGoogle Scholar
  21. 21.
    Curd FHS, Landquist JK, Rose FL (1947) J Chem Soc 6:775CrossRefGoogle Scholar
  22. 22.
    Thorat DA, Doddareddy MR, Seo SH, Hong TJ, Cho YS, Hahn JS, Pae AN (2011) Bioorg Med Chem Lett 21:1593CrossRefGoogle Scholar
  23. 23.
    Yan SJ, Zheng H, Huang C, Yan YY, Lin J (2010) Bioorg Med Chem Lett 20:4432CrossRefGoogle Scholar
  24. 24.
    Schwalbe CH, Williams GJB (1986) Acta Crystallogr C 42:1257CrossRefGoogle Scholar
  25. 25.
    Kurtz HA, Stewart JJP, Dieter KM (1990) J Comput Chem 11:182CrossRefGoogle Scholar
  26. 26.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery, Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford CTGoogle Scholar
  27. 27.
    Thanthiriwatte KS, Nalin de Silva KM (2002) J Mol Struct Theochem 617:169CrossRefGoogle Scholar
  28. 28.
    Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA Jr (1993) J Comput Chem 14:1347CrossRefGoogle Scholar
  29. 29.
    Altomare A, Burla MC, Camalli M, Cascarano G, Giacovazzo C, Guagliardi A, Polidori G (1994) J Appl Crystallogr 27:435Google Scholar
  30. 30.
    Sheldrick GM (2008) Acta Crystallogr A64:112Google Scholar
  31. 31.
    Karakaş A, Elmali A, Ünver H, Svoboda I (2004) J Mol Struct 702:103CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Michaela Fridrichová
    • 1
  • Ivan Němec
    • 1
  • Ivana Císařová
    • 1
  • Nad’a Tesařová
    • 2
  • Petr Němec
    • 2
  • Aslı Karakaş
    • 3
  • Nihal Kahraman
    • 3
  • Mehmet Taşer
    • 3
  1. 1.Department of Inorganic Chemistry, Faculty of ScienceCharles University in PraguePrague 2Czech Republic
  2. 2.Department of Chemical Physics and Optics, Faculty of Mathematics and PhysicsCharles University in PraguePrague 2Czech Republic
  3. 3.Department of Physics, Faculty of SciencesSelçuk UniversityKonyaTurkey

Personalised recommendations