Table of Contents
ISRN Organic Chemistry
Volume 2011, Article ID 589012, 10 pages
http://dx.doi.org/10.5402/2011/589012
Research Article

Linear and Angular Distyrylpyrazines with Terminal Donor Groups: Synthesis, Solvatochromism, and Acidochromism of the Electronic Spectra

Institute for Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55099 Mainz, Germany

Received 29 January 2011; Accepted 7 March 2011

Academic Editors: C. F. Chen and F. C. Pigge

Copyright © 2011 Volker Schmitt et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. K. Müllen and G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, Germany, 1998.
  2. U. Stalmach, H. Detert, H. Meier et al., “Relationship between structure and electroluminescence of oligo(p-phenylenevinylene)s,” Optical Materials, vol. 9, no. 1-4, pp. 77–81, 1998. View at Google Scholar · View at Scopus
  3. U. Stalmach and H. Detert, “Synthesis and electronic spectra of substituted p-distyrylbenzenes for the use in light-emitting diodes,” Advanced Synthesis and Catalysis, vol. 342, no. 1, pp. 10–16, 2000. View at Google Scholar · View at Scopus
  4. M. Nohara, M. Hasegawa, C. Hosokawa, H. Tokailin, and T. Kusumoto, “A new series of electroluminescent organic compounds,” Chemistry Letters, pp. 189–190, 1990. View at Google Scholar
  5. M. W. Liu, X. H. Zhang, W. Y. Lai et al., “A new series of blue emitting pyrazine derivatives for prganic electroluminescence devices,” Physica Status Solidi A, vol. 185, no. 2, pp. 203–211, 2001. View at Publisher · View at Google Scholar · View at Scopus
  6. A. Wu, T. Akagi, M. Jikei et al., “New fluorescent polyimides for electroluminescent devices based on 2,5-distyrylpyrazine,” Thin Solid Films, vol. 273, no. 1-2, pp. 214–217, 1996. View at Google Scholar · View at Scopus
  7. S. Achelle, I. Nouira, B. Pfaffinger, Y. Ramondenc, N. Plé, and J. Rodríguez-López, “V-shaped 4,6-bis(arylvinyl)pyrimidine oligomers: synthesis and optical properties,” Journal of Organic Chemistry, vol. 74, no. 10, pp. 3711–3717, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Kraft, A. C. Grimsdale, and A. B. Holmes, “Elektrolumineszierende konjugierte Polymere Polymere erstrahlen inneuem Licht,” Angewandte Chemie, vol. 110, pp. 416–443, 1998, Angewandte Chemie International Edition, vol. 37, pp. 402–428. View at Google Scholar
  9. H. Detert and E. Sugiono, “Stilbenoid phosphors with increased electron affinity: sulfones as electron accepting groups,” Synthetic Metals, vol. 122, no. 1, pp. 15–17, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. H. Detert, D. Schollmeyer, and E. Sugiono, “Synthesis, structure and solvatochromism of the emission of cyano-substituted oligo(phenylenevinylene)s,” European Journal of Organic Chemistry, no. 15, pp. 2927–2938, 2001. View at Google Scholar · View at Scopus
  11. B. Lange, R. Zentel, C. Ober, and S. Marder, “Photoprocessable polymer opals,” Chemistry of Materials, vol. 16, no. 25, pp. 5286–5292, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. B. Strehmel, A. M. Sarker, and H. Detert, “The influence of σ and π acceptors on two-photon absorption and solvatochromism of dipolar and quadrupolar unsaturated organic compounds,” ChemPhysChem, vol. 4, no. 3, pp. 249–259, 2003. View at Publisher · View at Google Scholar · View at Scopus
  13. J. Schoönhaber, W. Frank, and T. J. J. Muöller, “Insertion-coupling-cycloisomerization domino synthesis and cation-induced halochromic fluorescence of 2,4-diarylpyrano[2,3-b]indoles,” Organic Letters, vol. 12, no. 18, pp. 4122–4125, 2010. View at Publisher · View at Google Scholar
  14. J. Y. Jaung, “Synthesis and halochromism of new quinoxaline fluorescent dyes,” Dyes and Pigments, vol. 71, no. 3, pp. 245–250, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. H. I. X. Mager and W. Berends, “Pyrazine derivatives—II. Preparation of pyrazine-2,3,5-tricarboxylic acid and of pyrazine-2,5- and -2,6-dicarboxylic acids,” Recueil des Travaux Chimiques des Pays-Bas, vol. 77, pp. 827–841, 2000. View at Google Scholar
  16. L. Scaccianoce, N. Feeder, S. J. Teat, E. A. Marseglia, A. C. Grimsdale, and A. B. Holmes, “Synchrotron diffraction study of two polymorphic forms of 2,5-bis-[2-(4-methoxyphenyl)ethenyl]pyrazine,” Acta Crystallographica. Section C, vol. 56, no. 10, pp. 1277–1279, 2000. View at Publisher · View at Google Scholar · View at Scopus
  17. S.-Y. An, S.-D. Xu, Q.-D. Zeng et al., “The self-assembly structure of pyrazine derivative on highly oriented pyrolytic graphite,” Wuli Huaxue Xuebao, vol. 21, no. 8, pp. 925–928, 2005. View at Google Scholar
  18. S. M. Al-Hazmy, A. S. Babaqi, E. Daltrozzo, M. Klink, J. Sauter, and E. M. Ebeid, “A new diolefinic laser dye: 2,5-bis-2-(2-naphthyl) vinyl pyrazine (B2NVP),” Journal of Photochemistry and Photobiology A, vol. 122, no. 1, pp. 17–22, 1999. View at Google Scholar · View at Scopus
  19. S. A. El-Daly, E. Z. M. Ebeid, S. M. El-Hazmy, A. S. Babaqi, Z. El-Gohary, and G. Duportail, “The spectra, lifetime and laser activity of 2,5-bis-2(l-naphthyl) vinylpyrazine and 2,5-bis-2(2-naphthyl)vinylpyrazine,” Journal of Chemical Sciences, vol. 105, no. 6, pp. 651–658, 1993. View at Publisher · View at Google Scholar · View at Scopus
  20. J. C. Collette and A. W. Harper, “Properties and chemical environment effects of alkylamino styryl pyrazine two-photon fluorophores,” in Linear and Nonlinear Optics of Organic Materials III, vol. 5212 of Proceedings of SPIE, pp. 184–192, 2003.
  21. T. Teshirogi, “2,5-Distyrylpyrazine derivatives as photosensitive monomers and their preparation,” Japanese Kokai Tokkyo Koho, 1989.
  22. G. Zerban, Styrylsubstituierte Aromaten mit langen Alkoxyseitenketten, Ph.D. thesis, Mainz, Germany, 1991.
  23. J. J. Vanden Eynde, L. Pascal, Y. Van Haverbeke, and P. Dubois, “Quaternary ammonium salt-assisted synthesis of extended π-systems from methyldiazines and aromatic aldehydes,” Synthetic Communications, vol. 31, no. 20, pp. 3167–3173, 2001. View at Publisher · View at Google Scholar · View at Scopus
  24. H. Lindauer, P. Czerney, and U.-W. Grummt, “9-(4-Dialkylaminostyryl)-acridines—a new class of acidochromic dyes,” Journal für Praktische Chemie, vol. 336, pp. 521–524, 1994. View at Google Scholar
  25. C. J. Kelley, K. Ansu, W. Budisusetyo, A. Ghiorghis, Y. Qin, and J. M. Kauffman, “Syntheses and photophysical properties of some 4-arylpyridinium salts,” Journal of Heterocyclic Chemistry, vol. 38, no. 1, pp. 11–23, 2001. View at Google Scholar · View at Scopus
  26. C. Lambert, S. Stadler, G. Bourhill, and C. Bräuchle, “Polarisierte π-Elektronensysteme in einem chemisch erzeugten elektrischen Feld: nichtlineare optische Eigenschaften zweiter Ordnung von Ammonium-Borat-Zwitterionen,” Angewandte Chemie, vol. 108, pp. 710–712, 1996, Angewandte Chemie International Edition, vol. 35, pp. 644–646. View at Google Scholar
  27. J. N. Wilson and U. H. F. Bunz, “Switching of intramolecular charge transfer in cruciforms: metal ion sensing,” Journal of the American Chemical Society, vol. 127, no. 12, pp. 4124–4125, 2005. View at Publisher · View at Google Scholar · View at Scopus
  28. H. Detert and E. Sugiono, “Bis(pyridylvinyl)diaminobenzenes: synthesis, acidochromism and solvatochromism of the fluorescence,” Journal of Luminescence, vol. 112, no. 1, pp. 372–376, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. P. Czerney and U. W. Grummt, “New near-infrared-absorbing acidochromic dyes and their application in sensor techniques,” Sensors and Actuators B, vol. 39, no. 1–3, pp. 395–400, 1997. View at Google Scholar · View at Scopus
  30. A. J. Zucchero, J. Tolosa, L. M. Tolbert, and U. H. F. Bunz, “Bis(4'-dibutylaminostyryl)benzene: spectroscopic behavior upon protonation or methylation,” Chemistry, vol. 15, no. 47, pp. 13075–13081, 2009. View at Publisher · View at Google Scholar · View at Scopus
  31. S. M. Brombosz, A. J. Zucchero, P. L. McGrier, and U. H. F. Bunz, “Acidochromicity of bisarylethynylbenzenes: hydroxy versus dialkylamino substituents,” Journal of Organic Chemistry, vol. 74, no. 23, pp. 8909–8913, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. V. Schmitt, S. Glang, J. Preis, and H. Detert, “Proton-induced multiple changes of the absorption and fluorescence spectra of amino-aza-oligo-(phenylenevinylene)s,” Advanced Sciences and Technologies, vol. 55, pp. 36–41, 2008. View at Google Scholar
  33. N. A. Nemkovich, Y. V. Kruchenok, A. N. Sobchuk, H. Detert, N. Wrobel, and E. A. Chernyavskii, “Subnanosecond spectrofluorimetry of new indolocarbazole derivatives in solutions and protein complexes and their dipole moments,” Optics and Spectroscopy, vol. 107, no. 2, pp. 275–281, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. N. A. Nemkovich, H. Detert, and V. Schmitt, “Localized excitation effect on dipole moments of oligophenylenevinylenes in their excited Franck-Condon state,” Chemical Physics, vol. 378, no. 1-3, pp. 37–41, 2010. View at Publisher · View at Google Scholar
  35. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, Germany, 2003.
  36. T. Eicher and S. Hauptmann, Chemie der Heterocyclen, Thieme, Stuttgart, Germany, 1994.
  37. K. Breitschwerdt, TH. Förster, and A. Weller, “Absorptionsspektroskopischer Nachweis der elektrolytischen Dissoziation angeregter Molekeln,” Die Naturwissenschaften, vol. 43, no. 19, p. 443, 1956. View at Publisher · View at Google Scholar · View at Scopus
  38. H. Detert and E. Sugiono, “Synthesis, electronic spectra and photochemical behaviour of oligo(phenylenevinylene)s with electron-withdrawing substituents,” Journal of Physical Organic Chemistry, vol. 13, pp. 587–561, 2000. View at Google Scholar
  39. X. M. Wang, Y. F. Zhou, W. T. Yu et al., “Two-photon pumped lasing stilbene-type chromophores containing various terminal donor groups: relationship between lasing efficiency and intramolecular charge transfer,” Journal of Materials Chemistry, vol. 10, no. 12, pp. 2698–2703, 2000. View at Publisher · View at Google Scholar · View at Scopus