Two-photon absorption and piezofluorochromism of aggregation-enhanced emission 2,6-bis(p-dibutylaminostyryl)-9,10-bis(4-pyridylvinyl-2)anthracene

Dyes and Pigments

Volumn 113, Issue , 2015, Pages 307-311

  Zhang, Deteng ^a   Gao, Yangyang ^a   Dong, Jing ^a   Sun, Qikun ^a   Liu, Wei ^a   Xue, Shanfeng ^a   Yang, Wenjun ^a  

^a QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

2,6,9,10 tetravinylanthracene derivative; Aggregation enhanced emission; Cruciform dye; Piezofluorochromism; Solvatochromic effect; Two photon absorption

Indexed keywords

ANTHRACENE; DICHLOROMETHANE; EMISSION SPECTROSCOPY; FLUORESCENCE; PHOTONS; SOLS; X RAY DIFFRACTION;

DIFFERENTIAL SCANNING CALORIMETRIC ANALYSIS; ENHANCED EMISSION; INDUCED PHASE TRANSFORMATION; PIEZOFLUOROCHROMISM; SOLVATOCHROMIC EFFECTS; TWO PHOTON ABSORPTION; TWO-PHOTON ABSORPTION CROSS SECTION; WIDE ANGLE XRAY DIFFRACTION;

TWO PHOTON PROCESSES;

EID: 84907224640     PISSN: 01437208     EISSN: 18733743     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.08.025     Document Type: Article

References (40)

1. Ding D, Li K, Liu B, Tang BZ. Bioprobes based on AIE fluorogens. Acc Chem Res 2013;46:2441-53.
2. Qin W, Liu J, Chen S, Lam Jacky WY, Arseneault M, Yang Z, et al. Crafting NPB with tetraphenylethene: a winewin strategy to create stable and efficient solid-state emitters with aggregation-induced emission feature, high hole-transporting property and efficient electroluminescence. J Mater Chem C 2014;2:3756-61.
3. Sagara Y, Kato T. Mechanically induced luminescence changes in molecular assemblies. Nat Chem 2009;1:605-10.
4. Weder C. Mechanoresponsive materials. J Mater Chem 2011;21:8235-6.
5. Chi Z, Zhang X, Xu B, Zhou X, Ma C, Zhang Y, et al. Recent advances in organic mechanofluorochromic materials. Chem Soc Rev 2012;41:3878-96.
6. Chen X, Shen X, Guan E, Liu Y, Qin A, Sun J, et al. A pyridinyl-functionalized tetraphenylethylene fluorogen for specifically sensing trivalent cations. Chem Commun 2013;49:1503-5.
7. Dong Y, Xu B, Zhang J, Tan X, Wang L, Chen J, et al. Piezochromic luminescence based on the molecular aggregation of 9, 10-bis((E)-2-(pyrid-2-yl)vinyl) anthracene. Angew Chem Int Ed 2012;51:10782-5.
8. Gong Y, Tan Y, Liu J, Lu P, Feng C, Yuan W, et al. Twisted DepeA solid emitters: efficient emission and high contrast mechanochromism. Chem Commun 2013;49:4009-11.
9. (a) Zhang X, Chi Z, Zhang J, Li H, Xu B, Li X, et al. Piezofluorochromic properties and mechanism of an aggregation-induced emission enhancement compound containing N-hexylphenothiazine and anthracene moieties. J Phys Chem B 2011;23:7606-11
10. (b) Liu W, Wang Y, Sun M, Zhang D, Zheng M, Yang W. Alkoxy-position effects on piezofluorochromism and aggregation-induced emission of 9, 10-bis(alkoxystyryl)anthracenes. Chem Commun 2013;49:6042-4.
11. (a) Liang J, Hu F, Lv X, Chen Z, Chen Z, Yin J. Synthesis, characterization and mechanochromic behavior of binuclear gold(I) complexes with various diiso-cyano bridges. Dyes Pigments 2012;95:485-90
12. (b) Mizuguchi K, Nakano H. Mechanofluorochromism of 4-[bis(9, 9-dimethylfluoren-2-yl)amino]benz-aldehyde. Dyes Pigm 2013;96:76-80.
13. Kim S, Zheng Q, He G, Bharali D, Pudavar H, Baev A, et al. Aggregation-enhanced fluorescence and two-photon absorption in nano-aggregates of a 9, 10-bis[40-(400-aminostyryl)styryl]anthracene derivative. Adv Funct Mater 2006;16:2317-23.
14. Wang B, Wang Y, Hua J, Jiang Y, Huang J, Qian S, et al. Starburst triarylamine donoreacceptoredonor quadrupolar derivatives based on cyano-substituted diphenylaminestyrylbenzene: tunable aggregation-induced emission colors and large two-photon absorption cross sections. Chem Eur J 2011;17: 2647-55.
15. Jiang Y, Wang Y, Hua J, Tang J, Li B, Qian S, et al. Multibranched triarylamine end-capped triazines with aggregation-induced emission and large two-photon absorption cross-sections. Chem Commun 2010;46:4689-91.
16. Wang Y, Liu T, Bu L, Li J, Yang C, Li X, et al. Aqueous nano-aggregation-enhanced one-and two-photon fluorescence, crystalline J-aggregation-induced red shift, and amplified spontaneous emission of 9, 10-bis(p-dime-thylaminostyryl)-anthracene. J Phys Chem C 2012;116:15576-83.
17. Noh S, Kim R, Kim W, Kim S, Lee K, Cho N, et al. Aggregation-enhanced two-photon absorption and up-converted fluorescence of quadrupolar 1, 4-bis(cyanostyryl)-benzene derivatives showing solvatochromic fluorescence. J Mater Chem 2010;20:7422-9.
18. Zhang H, Guo E, Zhang Y, Ren P, Yang W. Donoreacceptor-substituted anthracene-centered cruciforms: synthesis, enhanced two-photon absorptions, and spatially separated frontier molecular orbitals. Chem Mater 2009;21:5125-35.
19. Sun M, Zhang D, Li Y, Wang J, Gao Y, Yang W. Aggregation-enhanced emission and piezochromic luminescence of 9, 10-bis(p-dibutylaminostyryl)-2, 6-bis(p-t-butylstyryl)anthracene. J Lumin 2014;148:55-9.
20. Zheng M, Sun M, Li Y, Wang J, Bu L, Xue S, et al. Piezofluorochromic properties of AIE-active 9, 10-bis(N-alkylphenothiazin-3-yl-vinyl-2)anthracenes with different length of alkyl chains. Dyes Pigm 2014;102:29-34.
21. (a) Li J, Liu T, Zheng M, Sun M, Zhang D, Zhang H, et al. Dibutylaminophenyl-and/or pyridinyl-capped 2, 6, 9, 10-tetravinylanthracene cruciforms: synthesis and aggregation-enhanced one-and two-photon excited fluorescence. J Phys Chem C 2013;117:8404-10
22. (b) Zheng M, Sun M, Zhang D, Liu T, Xue S, Yang W. Fluorescence response of pyridinyl-and/or dibutylaniline-capped 2, 6, 9, 10-tetra-vinylanthracenes to metal ions. Dyes Pigm 2014;101:109-15.
23. Xu B, Xie M, He J, Xu B, Chi Z, Tian W, et al. An aggregation-induced emission lumino-phore with multi-stimuli single-and two-photon fluorescence switching and large two-photon absorption cross section. Chem Commun 2013;49:273-5.
24. Kang H, Evmenenko G, Dutta P, Clays K, Song K, Marks T. X-shaped electro-optic chromophore with remarkably blue-shifted optical absorption. Synthesis, characterization, linear/nonlinear optical properties, self-assembly, and thin film microstructural characteristics. J Am Chem Soc 2006;128:6194-205.
25. Sun X, Liu Y, Chen S, Qiu W, Yu G, Ma Y, et al. X-shaped electroactive molecular materials based on oligothioph architectures: facile synthesis and photophysical and electrochemical properties. Adv Funct Mater 2006;16: 917-25.
26. Wilson J, Smith M, Enkelmann V, Bunz U. Cruciform p-systems: effect of aggregation on emission. Chem Commun 2004:1700-1.
27. Zhou N, Wang L, Thompson D, Zhao Y. Synthesis, electronic, and photo-physical properties of cruciform OPE/OPV hybrid oligomer bridged bisfuller-ene triads. Tetrahedron Lett 2007;48:3563-7.
28. Wang H, Feng J, Wen G, Jiang H, Wan J, Zhu R, et al. Cruciform pen diblock conjugated oligomers for electroluminescent applications. New J Chem 2006;30:667-70.
29. Spitler E, Shirtcliff L, Halley M. Systematic structureeproperty investigations and ion-sensing studies of pyridine-derivatized donor/acceptor tetrakis(ar-ylethynyl)benzenes. J Org Chem 2007;72:86-96.
30. Marsden J, Miller J, Shirtcliff L, Haley M. Structureeproperty relationships of donor/acceptor-functionalized tetrakis(phenylethynyl)benzenes and bis(de-hydro-benzoannuleno)benzenes. J Am Chem Soc 2005;127:2464-76.
31. Zucchero A, Wilson J, Bunz U. Cruciforms as functional fluorophores: response to protons and selected metal ions. J Am Chem Soc 2006;128:11872-81.
32. (a) Wilson J, Bunz U. Switching of intramolecular charge transfer in cruci-forms: metal ion sensing. J Am Chem Soc 2005;127:4124-5
33. (b) Zucchero A, Mcgrier P, Bunz U. Cross-conjugated cruciform fluorophores. Acc Chem Res 2010;43:397-408.
34. Demas J, Crosby G. The measurement of photoluminescence quantum yields. J Phys Chem 1975;74. 991-1021.
35. Rumi M, Ehrlich J, Heikal A, Perry J, Barlow S, Hu Z, et al. Structureeproperty relationships for two-photon absorbing chromophores: bis-donor diphenyl-polyene and bis(styryl)benzene derivatives. J Am Chem Soc 2000;122: 9500-10.
36. Cho B, Son K, Lee S, Song Y, Lee Y, Jeon S, et al. Two photon absorption properties of 1, 3, 5-tricyano-2, 4, 6-tris(styryl)benzene derivatives. J Am Chem Soc 2001;123:10039-45.
37. Guo E, Ren P, Zhang Y, Zhang H, Yang W. Diphenylamine end-capped 1, 4-diketo-3, 6-diphenylpyrrolo[3, 4-c]pyrrole derivatives with large two-photon absorption cross sections and strong two-photon excitation red fluorescence. Chem Commun 2009:5859-61.
38. Xu C, Webb W. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B 1996;13:481-91.
39. Bairu S, Ramakrishna G. Two-photon absorption properties of chromophores in micelles: electrostatic interactions. J Phys Chem B 2013;117:10484-91.
40. Woo H, Liu B, Kohler B, Korystov D, Mikhailovsky A, Bazan G. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J Am Chem Soc 2005;127:14721-9.