Table of Contents Author Guidelines Submit a Manuscript
International Journal of Photoenergy
Volume 2014 (2014), Article ID 124753, 9 pages
http://dx.doi.org/10.1155/2014/124753
Research Article

A White-Light-Emitting Small Molecule: Synthesis, Crystal Structure, and Optical Properties

Department of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan

Received 21 December 2013; Accepted 30 January 2014; Published 26 May 2014

Academic Editor: David Lee Phillips

Copyright © 2014 Sin-Kai Fang 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. J. Zhao, S. Ji, Y. Chen, H. Guo, and P. Yang, “Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials,” Physical Chemistry Chemical Physics, vol. 14, no. 25, pp. 8803–8817, 2012. View at Publisher · View at Google Scholar · View at Scopus
  2. M. A. Satam, R. K. Raut, R. D. Telore, and N. Sekar, “Fluorescent acid azo dyes from 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol and comparison with 2-naphthol analogs,” Dyes and Pigments, vol. 97, no. 1, pp. 32–42, 2013. View at Publisher · View at Google Scholar · View at Scopus
  3. L. Xie, Y. Chen, W. Wu, H. Guo, J. Zhao, and X. Yu, “Fluorescent coumarin derivatives with large stokes shift, dual emission and solid state luminescent properties: an experimental and theoretical study,” Dyes and Pigments, vol. 92, no. 3, pp. 1361–1369, 2012. View at Publisher · View at Google Scholar · View at Scopus
  4. P. Yang, J. Zhao, W. Wu, X. Yu, and Y. Liu, “Accessing the long-lived triplet excited states in bodipy-conjugated 2-(2-hydroxyphenyl) benzothiazole/benzoxazoles and applications as organic triplet photosensitizers for photooxidations,” Journal of Organic Chemistry, vol. 77, no. 14, pp. 6166–6178, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. M. A. Satam, R. K. Raut, and N. Sekar, “Fluorescent azo disperse dyes from 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol and comparison with 2-naphthol analogs,” Dyes and Pigments, vol. 96, no. 1, pp. 92–103, 2013. View at Publisher · View at Google Scholar · View at Scopus
  6. Z. Q. Guo, W. Q. Chen, and X. M. Duan, “Seven-membered ring excited-state intramolecular proton-transfer in 2-benzamido-3-(pyridin-2-yl)acrylic acid,” Dyes and Pigments, vol. 92, no. 1, pp. 619–625, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. J. E. Kwon, S. Park, and S. Y. Park, “Realizing molecular pixel system for full-color fluorescence reproduction: RGB-emitting molecular mixture free from energy transfer crosstalk,” Journal of the American Chemical Society, vol. 135, no. 30, pp. 11239–11246, 2013. View at Publisher · View at Google Scholar
  8. M. H. Luo, H. Y. Tsai, H. Y. Lin, S. K. Fang, and K. Y. Chen, “Extensive spectral tuning of the proton transfer emission from green to red via a rational derivatization of salicylideneaniline,” Chinese Chemical Letters, vol. 23, no. 11, pp. 1279–1282, 2012. View at Publisher · View at Google Scholar · View at Scopus
  9. T. C. Fang, H. Y. Tsai, M. H. Luo, C. Chang, and K. Chen, “Excited-state charge coupled proton transfer reaction via the dipolar functionality of salicylideneaniline,” Chinese Chemical Letters, vol. 24, no. 2, pp. 145–148, 2013. View at Publisher · View at Google Scholar · View at Scopus
  10. A. U. Khan and M. Kasha, “Mechanism of four-level laser action in solution excimer and excited-state proton-transfer cases,” Proceedings of the National Academy of Sciences of the United States of America, vol. 80, no. 6, pp. 1767–1770, 1983. View at Publisher · View at Google Scholar
  11. W. H. Chen and Y. Pang, “Excited-state intramolecular proton transfer in 2-(2′,6′-dihydroxyphenyl)benzoxazole: effect of dual hydrogen bonding on the optical properties,” Tetrahedron Letters, vol. 51, no. 14, pp. 1914–1918, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. G. O. W. Lins, L. F. Campo, F. S. Rodembusch, and V. Stefani, “Novel ESIPT fluorescent benzazolyl-4-quinolones: synthesis, spectroscopic characterization and photophysical properties,” Dyes and Pigments, vol. 84, no. 1, pp. 114–120, 2010. View at Publisher · View at Google Scholar · View at Scopus
  13. C. K. Lim, J. Seo, S. Kim, I. C. Kwon, C. Ahn, and S. Y. Park, “Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile,” Dyes and Pigments, vol. 90, no. 3, pp. 284–289, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. C. M. Maupin, N. Castillo, S. Taraphder et al., “Chemical rescue of enzymes: proton transfer in mutants of human carbonic anhydrase II,” Journal of the American Chemical Society, vol. 133, no. 16, pp. 6223–6234, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. Y. Ito, K. Amimoto, and T. Kawato, “Prototropic tautomerism and solid-state photochromism of N-phenyl-2-aminotropones,” Dyes and Pigments, vol. 89, no. 3, pp. 319–323, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. R. C. D. Santos, N. V. D. S. Faleiro, L. F. Campo et al., “Synthesis and photophysical properties of novel succinimidyl benzazole derivatives, evaluated by Candida albicans ATCC 10231 fluorescent staining,” Tetrahedron Letters, vol. 52, no. 23, pp. 3048–3053, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. T. Li, Z. Yang, Y. Li, Z. Liu, G. Qi, and B. Wang, “A novel fluorescein derivative as a colorimetric chemosensor for detecting copper(II) ion,” Dyes and Pigments, vol. 88, no. 1, pp. 103–108, 2011. View at Publisher · View at Google Scholar · View at Scopus
  18. Y. J. Zhang, X. P. He, M. Hu, Z. Li, X. Shi, and G. Chen, “Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone,” Dyes and Pigments, vol. 88, no. 3, pp. 391–395, 2011. View at Publisher · View at Google Scholar · View at Scopus
  19. W. H. Hong, C. C. Lin, T. S. Hsieh, and C. Chang, “Preparation of fluoroionophores based on diamine-salicylaldehyde derivatives,” Dyes and Pigments, vol. 94, no. 3, pp. 371–379, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. Q. Huang, X. F. Yang, and H. Li, “A ratiometric fluorescent probe for hydrogen sulfide based on an excited-state intramolecular proton transfer mechanism,” Dyes and Pigments, vol. 99, no. 3, pp. 871–877, 2013. View at Publisher · View at Google Scholar
  21. S. Ikeda, M. Toganoh, S. Easwaramoorthi, J. M. Lim, D. Kim, and H. Furuta, “Synthesis and photophysical properties of N-fused tetraphenylporphyrin derivatives: near-infrared organic dye of [18]annulenic compounds,” Journal of Organic Chemistry, vol. 75, no. 24, pp. 8637–8649, 2010. View at Publisher · View at Google Scholar · View at Scopus
  22. M. Ashraf, A. Teshome, A. J. Kay et al., “Synthesis and optical properties of NLO chromophores containing an indoline donor and azo linker,” Dyes and Pigments, vol. 95, no. 3, pp. 455–464, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. J. E. Kwon and S. Y. Park, “Advanced organic optoelectronic materials: harnessing excited-state intramolecular proton transfer (ESIPT) process,” Advanced Materials, vol. 23, no. 32, pp. 3615–3642, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. S. Park, J. Seo, S. H. Kim, and S. Y. Park, “Tetraphenylimidazole-based excited-state intramolecular proton-transfer molecules for highly efficient blue electroluminescence,” Advanced Functional Materials, vol. 18, no. 5, pp. 726–731, 2008. View at Publisher · View at Google Scholar · View at Scopus
  25. W. T. Chuang, C. C. Hsieh, C. H. Lai et al., “Excited-state intramolecular proton transfer molecules bearing o-hydroxy analogues of green fluorescent protein chromophore,” Journal of Organic Chemistry, vol. 76, no. 20, pp. 8189–8202, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. M. Mazzeo, V. Vitale, F. Della Sala et al., “Bright white organic light-emitting devices from a single active molecular material,” Advanced Materials, vol. 17, no. 1, pp. 34–39, 2005. View at Publisher · View at Google Scholar · View at Scopus
  27. Y. Liu, M. Nishiura, Y. Wang, and Z. Hou, “π-conjugated aromatic enynes as a single-emitting component for white electroluminescence,” Journal of the American Chemical Society, vol. 128, no. 17, pp. 5592–5593, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. S. Park, E. K. Ji, H. K. Se et al., “A white-light-emitting molecule: frustrated energy transfer between constituent emitting centers,” Journal of the American Chemical Society, vol. 131, no. 39, pp. 14043–14049, 2009. View at Publisher · View at Google Scholar · View at Scopus
  29. K. C. Tang, M. J. Chang, T. Y. Lin et al., “Fine tuning the energetics of excited-state intramolecular proton transfer (ESIPT): white light generation in a single ESIPT system,” Journal of the American Chemical Society, vol. 133, no. 44, pp. 17738–17745, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. S. Kim, J. Seo, H. K. Jung, J. Kim, and S. Y. Park, “White luminescence from polymer thin films containing excited-state intramolecular proton-transfer dyes,” Advanced Materials, vol. 17, no. 17, pp. 2077–2082, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. G. M. Sheldrick, SHELXS97, a Program for Automatic Solution of Crystal Structure, University of Göttingen, Göttingen, Germany, 1997.
  32. G. M. Sheldrick, SHELX97, a Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
  33. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 03, Gaussian, Inc., Pittsburgh, Pa, USA, 2003.
  34. M. Koné, B. Illien, J. Graton, and C. Laurence, “B3LYP and MP2 calculations of the enthalpies of hydrogen-bonded complexes of methanol with neutral bases and anions: comparison with experimental data,” Journal of Physical Chemistry A, vol. 109, no. 51, pp. 11907–11913, 2005. View at Publisher · View at Google Scholar · View at Scopus
  35. T. Schaefer, “A relationship between hydroxyl proton chemical shifts and torsional frequencies in some ortho-substituted phenol derivatives,” Journal of Physical Chemistry, vol. 79, no. 17, pp. 1888–1890, 1975. View at Google Scholar · View at Scopus
  36. K.-Y. Chen, Y.-M. Cheng, C.-H. Lai et al., “Ortho green fluorescence protein synthetic chromophore; excited-state intramolecular proton transfer via a seven-membered-ring hydrogen-bonding system,” Journal of the American Chemical Society, vol. 129, no. 15, pp. 4534–4535, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. K.-Y. Chen, C.-C. Hsieh, Y.-M. Cheng, C. Lai, and P. Chou, “Extensive spectral tuning of the proton transfer emission from 550 to 675 nm via a rational derivatization of 10-hydroxybenzo[h]quinoline,” Chemical Communications, no. 42, pp. 4395–4397, 2006. View at Publisher · View at Google Scholar · View at Scopus
  38. M. Zhang, D. Yang, B. Ren, and D. Wang, “A TDDFT study on the excited-state intramolecular proton transfer (ESIPT): excited-state equilibrium induced by electron density swing,” Journal of Fluorescence, vol. 23, no. 4, pp. 761–766, 2013. View at Publisher · View at Google Scholar · View at Scopus
  39. H.-Y. Tsai and K.-Y. Chen, “1,7-Diaminoperylene bisimides: synthesis, optical and electrochemical properties,” Dyes and Pigments, vol. 96, no. 2, pp. 319–327, 2013. View at Publisher · View at Google Scholar · View at Scopus