Cyanostilben-based derivatives: Mechanical stimuli-responsive luminophors with aggregation-induced emission enhancement

Photochemical and Photobiological Sciences

Volumn 11, Issue 9, 2012, Pages 1414-1421

  Zhang, Yujian ^a   Sun, Jingwei ^a   Bian, Gaofeng ^a,b   Chen, Yiyi ^a   Ouyang, Mi ^a   Hu, Bin ^a   Zhang, Cheng ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84865250887     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp05404c     Document Type: Article

References (45)

1. F. Würthner R. Sens K. H. Etzbach G. Seybold Design, synthesis, and evaluation of a dye library: glass-forming and solid-state luminescent merocyanines for functional materials Angew. Chem., Int. Ed. 1999 38 1649 1652
2. D. Oelkrug A. Tompert J. Gierschner H. J. Egelhaaf M. Hanack M. Hohloch E. Steinhuber Tuning of fluorescence in films and nanoparticles of oligophenylenevinylenes J. Phys. Chem. B 1998 102 1902 1907
3. W. S. Xia R. H. Schmehl C. J. Li A novel caesium selective fluorescent chemosensor Chem. Commun. 2000 695 696
4. Y. J. Hong W. Y. Lama B. Z. Tang Aggregation-induced emission: phenomenon, mechanism and applications Chem. Commun. 2009 4332 4353
5. B. K. An S. K. Kwon S. D. Jung S. Y. Park Enhanced emission and its switching in fluorescent organic nanoparticles J. Am. Chem. Soc. 2002 124 14410 14415
6. Y. J. Hong W. Y. Lama B. Z. Tang Aggregation-induced emission Chem. Soc. Rev. 2011 40 5361 5388
7. F. Würthner T. E. Kaiser C. R. Saha-Möller J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials Angew. Chem., Int. Ed. 2011 50 3376 3410
8. R. R. Hu E. Lager A. A. Aguilar J. Z. Liu J. W. Y. Lam H. H. Y. Sung I. D. Williams Y. C. Zhong K. S. Wong E. P. Cabrera B. Z. Tang Twisted intramolecular charge transfer and aggregation-induced emission of BODIPY derivatives J. Phys. Chem. C 2009 113 15845 15853
9. R. M. Adhikari B. K. Shah S. S. Palayangoda D. C. Neckers Solvent dependant optical switching in carbazole-based fluorescent nanoparticles Langmuir 2009 25 2402 2506
10. W. Rettig charge separation in excited states of decoupled systems-TICT compounds and implications regarding the development of new laser dyes and the primary process of vision and photosynthesis Angew. Chem., Int. Ed. Engl. 1986 25 971 988
11. U. Rösch S. Yao R. Wortmann F. Würthner Fluorescent H-aggregates of merocyanine dyes Angew. Chem., Int. Ed. 2006 45 7026 7030
12. Y. Sagara T. Kato Mechanically induced luminescence changes in molecular assemblies Nat. Chem. 2009 1 605 610
13. S. J. Yoon J. W. Chung J. Gierschner K. S. Kim M. G. Choi D. Kim S. Y. Park Multistimuli two-color luminescence switching via different slip-stacking of highly fluorescent molecular sheets J. Am. Chem. Soc. 2010 132 13675 13683
14. M. J. Teng X. R. Jia X. F. Chen Z. Y. Ma Y. Wei Mechanochromic luminescent property of a polypeptide-based dendron Chem. Commun. 2011 47 6078 6080
15. H. Bi D. Chen D. Li Y. Yuan D. D. Xia Z. L. Zhang H. Y. Zhang Y. Wang A green emissive amorphous fac-Alq3 solid generated by grinding crystalline blue fac-Alq3 powder Chem. Commun. 2011 47 4135 4137
16. A. L. Balch Dynamic crystals: visually detected mechanochemical changes in the luminescence of gold and other transition-metal complexes Angew. Chem., Int. Ed. 2009 48 2641 2644
17. S. Perruchas X. Goff S. Maron I. Maurin F. Guillen A. Garcia T. Gacoin J. P. Boilot Mechanochromic and thermochromic luminescence of a copper iodide cluster J. Am. Chem. Soc. 2010 132 10967 10969
18. G. Q. Zhang J. W. Lu C. L. Fraser Mechanochromic luminescence quenching: force-enhanced singlet-to-triplet intersystem crossing for iodide-substituted difluoroboron-dibenzoylmethane-dodecane in the solid state Inorg. Chem. 2010 49 10747 10749
19. H. Y. Li X. Q. Zhang Z. G. Chi B. J. Xu W. Zhou S. W. Liu Y. Zhang J. R. Xu New thermally stable piezofluorochromic aggregation-induced emission compounds Org. Lett. 2011 13 556 559
20. X. Q. Zhang Z. G. Chi J. Y. Zhang H. Y. Li B. J. Xu X. F. Li S. W. Liu Y. Zhang J. R. Xu Piezofluorochromic properties and mechanism of an aggregation-induced emission enhancement compound containing N-hexyl-phenothiazine and anthracene Moieties J. Phys. Chem. B 2011 115 7606 7611
21. X. Q. Zhang Z. G. Chi H. Y. Li B. J. Xu X. F. Li W. Zhou S. W. Liu Y. Zhang J. R. Xu Piezofluorochromism of an aggregation-induced emission compound derived from tetraphenylethylene Chem.-Asian J. 2011 6 808 811
22. Y. Shirota Organic materials for electronic and optoelectronic devices J. Mater. Chem. 2000 10 1 25
23. Y. F. Yue J. H. Kang M. X. Yu The synthesis and photophysical properties of novel triphenylamine derivatives containing α,β- diarylacrylonitrile Dyes Pigm. 2009 83 72 80
24. G. Qian B. Dai M. Luo D. B. Yu J. Zhan Z. Q. Zhang D. G. Ma Z. Y. Wang Band gap tunable, donor-acceptor-donor charge-transfer heteroquinoid-based chromophores: near infrared photoluminescence and electroluminescence Chem. Mater. 2008 20 6208 6216
25. N. Mataga Y. Kaifu M. Koizumi Solvent effects upon fluorescence spectra and the dipole moments of excited molecules Bull. Chem. Soc. Jpn. 1955 28 690 691
26. H. Auweter H. Haberkorn W. Heckmann D. Horn E. Lüddecke J. Rieger H. Weiss Supramolecular structure of precipitated nanosize beta-carotene particles Angew. Chem., Int. Ed. 1999 38 2188 2191
27. J. W. Chung B. K. An J. W. Kim J. J. Kim S. Y. Park Self-assembled perpendicular growth of organic nanoneedles via simple vapor-phase deposition: one-step fabrication of a superhydrophobic surface Chem. Commun. 2008 2998 3000
28. B. R. Gao H. Y. Wang Y. W. Hao L. M. Fu H. H. Fang Y. Jiang L. Wang Q. D. Chen H. Xia L. Y. Pan Y. G. Ma H. B. Sun Time-resolved fluorescence study of aggregation-induced emission enhancement by restriction of intramolecular charge transfer state J. Phys. Chem. B 2010 114 128 134
29. T. Hirose K. Matsuda Self-assembly of amphiphilic fluorescent dyes showing aggregate-induced enhanced emission: temperature dependence of molecular alignment and intermolecular interaction in aqueous environment Chem. Commun. 2009 5832 5834
30. K. A. N. Upamali L. A. Estrada P. K. De X. C. Cai J. A. Krause D. C. Neckers Carbazole-based cyano-stilbene highly fluorescent microcrystals Langmuir 2011 27 1573 1580
31. K. Itoh T. Azumi Shift of the emission band upon excitation at the long wavelength absorption edge: importance of the solute-solvent interaction and the solvent reorientation relaxation process J. Chem. Phys. 1975 62 3431 3439
32. A. Fletcher Fluorescence emission band shift with wavelength of excitation J. Phys. Chem. 1968 72 2742 2749
33. H. B. Fu J. N. Yao Size effects on the optical properties of organic nanoparticles J. Am. Chem. Soc. 2001 123 1434 1439
34. D. B. Xiao L. Xi W. S. Yang H. B. Fu Z. G. Shuai Y. Fang J. N. Yao Size-tunable emission from 1,3-diphenyl-5-(2-anthryl)-2-pyrazoline nanoparticles J. Am. Chem. Soc. 2003 125 6740 6745
35. A. Patra N. Hebalkar B. Sreedhar M. Sarkar A. Samanta T. P. Radhakrishnan Tuning the size and optical properties in molecular nano/microcrystals: manifestation of hierarchical interactions Small 2006 2 650 659
36. Y. Q. Dong J. W. Y. Lam A. J. Qin J. X. Sun J. Z. Liu Z. Li J. Z. Sun H. H. Y. Sung I. D. Williams H. S. Kwokc B. Z. Tang Aggregation-induced and crystallization-enhanced emissions of 1,2-diphenyl-3,4-bis(diphenylmethylene)-1- cyclobutene Chem. Commun. 2007 3255 3257
37. Y. Liu X. T. Tao F. Z. Wang J. H. Shi J. L. Sun W. T. Yu Y. Ren D. C. Zou M. H. Jiang Intermolecular hydrogen bonds induce highly emissive excimers: enhancement of solid-state luminescence J. Phys. Chem. C 2007 111 6544 6549
38. P. F. van Hutten V. V. Krasnikov H.-J. Brouwer G. Hadziioannou Excimer luminescence from single crystals and films of a cyano-substituted phenylene-vinylene model compound Chem. Phys. 1999 241 139 154
39. S. A. Jenekhe J. A. Osaheni Excimers and exciplexes of conjugated polymers Science 1994 265 765
40. Y. Liu X. T. Tao F. Z. Wang J. H. Shi J. L. Sun W. T. Yu Y. Ren D. C. Zou M. H. Jiang Intermolecular hydrogen bonds induce highly emissive excimers: enhancement of solid-state luminescence J. Phys. Chem. C 2007 111 6544 6549
41. P. F. van Hutten V. V. Krasnikov H.-J. Brouwer G. Hadziioannou Excimer luminescence from single crystals and films of a cyano-substituted phenylene-vinylene model compound Chem. Phys. 1999 241 139 154
42. R. A. Velapoldi H. H. Tonnesen Corrected emission spectra and quantum yields for a series of fluorescent compounds in the visible spectral region J. Fluoresc. 2004 14 465 472
43. G. A. Crosby J. N. Demas Measurement of photoluminescence quantum yields J. Phys. Chem. 1971 75 991 1024
44. H. Kasai H. Kamatani S. Okada H. Oikawa H. Matsuda H. Nakanishi Size-dependent colors and luminescences of organic microcrystals Jpn. J. Appl. Phys. 1996 35 L221 L223
45. H. B. Fu B. H. Loo D. B. Xiao R. M. Xie X. H. Ji J. N. Yao B. W. Zhang L. Q. Zhang Multiple emissions from 1,3-diphenyl-5- pyrenyl-2-pyrazoline nanoparticles: evolution from molecular to nanoscale to bulk materials Angew. Chem., Int. Ed. 2002 41 962 965