Aggregation-Induced Emission in Supramolecular π-Organogels

Aggregation-Induced Emission: Fundamentals and Applications

Volumn 1-2, Issue , 2013, Pages 233-251

  Xue, Pengchong ^a   Lu, Ran ^a  

^a Jilin University   (China)

Author keywords

Aggregation induced emission; Excited state intramolecular proton transfer; J aggregates; Planarity; Restricted intramolecular rotation; Twisted intermolecular charge transfer suppression; organogels

Indexed keywords

AGGREGATES; GELATION; ORGANIC POLYMERS; PROTON TRANSFER;

AGGREGATION-INDUCED EMISSIONS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; INTERMOLECULAR CHARGE TRANSFER; J AGGREGATES; ORGANOGELS; PLANARITY; RESTRICTED INTRAMOLECULAR ROTATION;

EXCITED STATES;

EID: 85014539433     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118735183.ch11     Document Type: Chapter

References (34)

1. Birks, J.B. (1970) Photophysics of Aromatic Molecules, Johjn Wiley & Sons, Ltd, London.
2. Valeur, B. (2002) Molecular Fluorescence: Principle and Applications, Wiley-VCH Verlag GmbH, Weinheim.
3. Borisov, S.M., and Wolfbeis, O.S. (2008) Optical biosensors. Chem. Rev., 108, 423-461.
4. Luo, J., Xie, Z., Lam, J.W.Y., Cheng, L., Chen, H., Qiu, C., Kwok, H.S., Zhan, X., Liu, Y., Zhu, D., and Tang, B.Z. (2001) Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole. Chem. Commun., 1740-1741.
5. Hong, Y., Lam, J.W.Y., and Tang, B.Z. (2009) Aggregation-induced emission: phenomenon, mechanism and applications. Chem. Commun. 4332-4353.
6. Hong, Y., Lam, J.W.Y., and Tang, B.Z. (2011) Aggregation-induced emission. Chem. Soc. Rev., 40, 5361-5388.
7. Terech, P., and Weiss, R.G. (1997) Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev., 97, 3133-3159.
8. Ajayaghosh, A., and Praveen, V.K. (2007) p-Organogels of self-assembled p-phenylenevinylenes: soft materials with distinct size, shape, and functions. Acc. Chem. Res., 40, 644-656.
9. Piepenbrock, M.M., Lloyd, G.O., Clarke, N., and Steed, J.W. (2010) Metal- and anion-binding supramolecular gels. Chem. Rev., 110, 1960-2004.
10. Bao, C.Y., Lu, R., Jin, M., Xue, P.C., Tan, C.H., Xu, T.H., Liu, G.F., and Zhao, Y.Y. (2006) Helical stacking tuned by alkoxy side chains in p-conjugated triphenylbenzene discotic derivatives. Chem. Eur. J., 12, 3287-3294.
11. An, B., Lee, D., Lee, J., Park, Y., Song, H., and Park, S.Y. (2004) Strongly fluorescent organogel system comprising fibrillar self-assembly of a trifluoromethyl-based cyanostilbene derivative. J. Am. Chem. Soc., 126, 10232-10233.
12. Chen, S.S., Li, T., and Zhao, D.H. (2010) Progress in discotic liquid crystalline materials. Acta. Phys.-Chim. Sin., 26, 1124-1134.
13. Hu, R., Lam, J.W.Y., Liu, J., Sung, H.H.Y., Williams, I.D., Yue, Z., Wong, K.S., Yuen, M.M.F., and Tang, B.Z. (2012) Hyperbranched conjugated poly(tetraphenylethene): synthesis, aggregation-induced emission, fluorescent photopatterning, optical limiting and explosive detection. Polym. Chem., 3, 1481-1489.
14. Li, Y., Li, F., Zhang, H., Xie, Z., Xie, W., Xu, H., Li, B., Shen, F., Ye, L., Hanif, M., Ma, D., and Ma, Y. (2007) Tight intermolecular packing through supramolecular interactions in crystals of cyano substituted oligo(para-phenylene vinylene): a key factor for aggregation-induced emission. Chem. Commun., 231-233.
15. Simalou, O., Zhao, X.G., Lu, R., Xue, P.C., Yang, X.C., and Zhang, X.F. (2009) Strategy to control the chromism and fluorescence emission of a perylene dye in composite organogel phases. Langmuir, 25, 11255-11260.
16. Ajayaghosh, A., Vijayakumar, C., Praveen, V.K., Babu, S.S., and Varghese, R. (2006) Self-location of acceptors as 'isolated' or 'stacked' energy traps in a supramolecular donor self-assembly: a strategy to wavelength tunable FRET emission. J. Am. Chem. Soc., 128, 7174-7175.
17. Ryu, S.Y., Kim, S., Seo, J., Kim, Y., Kwon, O., Jang, D., and Park, S.Y. (2004) Strong fluorescence emission induced by supramolecular assembly and gelation: luminescent organogel from nonemissive oxadiazole-based benzene-1, 3, 5-tricarboxamide gelator. Chem. Commun., 70-71.
18. Manna, S., Saha, A., and Nandi, A.K. (2006) A two component thermoreversible hydrogel of riboflavin and mela-mine: enhancement of photoluminescence in the gel form. Chem. Commun. 4285-4287.
19. Chung, J.W., An, B., and Park, S.Y. (2008) A thermoreversible and proton-induced gel-sol phase transition with remarkable fluorescence variation. Chem. Mater., 20, 6750-6755.
20. Xu, Y., Xue, P.C., Xu, D.F., Zhang, X.F., Liu, X.L., Zhou, H.P., Jia, J.H., Yang, X.C., Wang, F.Y., and Lu, R. (2010) Multicolor fluorescent switches in gel systems controlled by alkoxyl chain and solvent. Org. Biomol. Chem., 8, 4289-4296.
21. Bao, C.Y., Lu, R., Jin, M., Xue, P.C., Tan, C.H., Liu, G.F., and Zhao, Y.Y. (2005) L-Tartaric acid assisted binary organogel system: strongly enhanced fluorescence induced by supramolecular assembly. Org. Biomol. Chem., 3, 2508-2512.
22. Kim, T.H., Choi, M.S., Sohn, B., Park, S.Y., Lyood, W.S., and Lee, T.S. (2008) Gelation-induced fluorescence enhancement of benzoxazole-based organogel and its naked-eye fluoride detection. Chem. Commun., 2364-2366.
23. Kim, T.H., Kim, D.G., Lee, M., and Lee, T.S. (2010) Synthesis of reversible fluorescent organogel containing 2-(20-hydroxyphenyl)benzoxazole: fluorescence enhancement upon gelation and detecting property for nerve gas stimulant. Tetrahedron, 66, 1667-1672.
24. Yang, X.C., Lu, R., Zhou, H.P., Xue, P.C., Wang, F.Y., Chen, P., and Zhao, Y.Y. (2009) Aggregation-induced blue shift of fluorescence emission due to suppression of TICT in a phenothiazine-based organogel. J. Colloid Interface Sci., 330, 527-532.
25. Birkedal, H., and Pattison, P. (2006) Bis[4-(salicylideneamino)phenyl]methane. Acta Crystallogr., Sect. C: Cryst. Struct. Commun., C620139-0141.
26. Xue, P.C., Lu, R., Chen, G.J., Zhang, Y., Nomoto, H., Takafuji, M., and Ihara, H. (2007) Functional organogel based on a salicylideneaniline derivative with enhanced fluorescence emission and photochromism. Chem. Eur. J., 13, 8231-8239.
27. Chen, P., Lu, R., Xue, P.C., Xu, T.H., Chen, G.J., and Zhao, Y.Y. (2009) Emission enhancement and chromism in a salen-based gel system. Langmuir, 25, 8395-8399.
28. Tsou, C., and Sun, S. (2006) New fluorescent amide-functionalized phenylethynylthiophene low molecular weight gelator. Org. Lett., 8, 387-390.
29. Yang, H., Yi, T., Zhou, Z., Zhou, Y., Wu, J., Xu, M., Li, F., and Huang, C. (2007) Switchable fluorescent organogels and mesomorphic superstructure based on naphthalene derivatives. Langmuir, 23, 8224-8230.
30. Qian, Y., Li, S., Wang, Q., Sheng, X., Wu, S., Wang, S., Lia, J., and Yang, G. (2012) A nonpolymeric highly emissive ESIPT organogelator with neither dendritic structures nor long alkyl/alkoxy chains. Soft Matter, 8, 757-764.
31. Yang, X.C., Lu, R., Xu, T.H., Xue, P.C., Liu, X.L., and Zhao, Y.Y. (2008) Novel carbazole-based organogels modulated by tert-butyl moieties. Chem. Commun., 453-455.
32. Yang, X.C., Lu, R., Xue, P.C., Li, B., Xu, D.F., Xu, T.H., and Zhao, Y.Y. (2008) Carbazole-based organogel as a scaffold to construct energy transfer arrays with controllable fluorescence emission. Langmuir, 24, 13730-13735.
33. Xu, D.F., Liu, X.L., Lu, R., Xue, P.C., Zhang, X.F., Zhou, H.P., and Jia, J.H. (2011) New dendritic gelator bearing carbazole in each branching unit: selected response to fluoride ion in gel phase. Org. Biomol. Chem., 9, 1523-1528.
34. Chen, Y., Lv, Y., Han, Y., Zhu, B., Zhang, F., Bo, Z., and Liu, C.Y. (2009) Dendritic effect on supramolecular self-assembly: organogels with strong fluorescence emission induced by aggregation. Langmuir, 25, 8548-8555.