Recent Progress of Tetraphenylethenes with Aggregation-Induced Emission

doi:10.7517/j.issn.1674-0475.2012.01.9

Abstract

Abstract: Among the novel organic molecules with aggregation-induced emission (AIE), tetraphenylethenes (TPEs) enjoy the advantages of facile synthesis and efficient solid-state emission as well as high thermal stability. This review mainly focuses on the AIE properties of TPEs with the aspect of hydrophilicity or hydrophobicity.The relationship between TPEs' structures and AIE properties was explained. The application as bio- and chemo-sensors was introduced. Finally, a brief outlook on the design of new AIE-active TPEs and the application of them in relevant fields is forwarded.

Key words: tetraphenylethenes, aggregation-induced emission, bio- and chemo-sensors

CLC Number:

XIA Jing, WU Yan-mei, ZHANG Ya-ling, TONG Bing, SHI Jian-bing, ZHI Jun-ge, DONG Yu-ping. Recent Progress of Tetraphenylethenes with Aggregation-Induced Emission[J]. Imaging Science and Photochemistry, 2012, 30(1): 9-25.

References

[1] An B K, Kwon S K, Jung S D, Park S Y. Enhanced emission and its switching in fluorescent organic nanoparticles[J]. J. Amer. Chem. Soc., 2002, 124(48): 14410-14415.
[2] Tracy H J, Mullin J L, Klooster W T, Martin J A, Haug J, Wallace S, Rudloe I, Watts K. Enhanced photoluminescence from group 14 metalloles in aggregated and solid solutions[J]. Inorg. Chem., 2005, 44(6): 2003-2011.
[3] Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Kwok H S, Zhan X W, Liu Y Q, Zhu D B, Tang B Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chem. Commun., 2001, (18): 1740-1741.
[4] Tang B Z, Zhan X W, Yu G, Lee P P S, Liu Y Q, Zhu D B. Efficient blue emission from siloles[J]. J. Mater. Chem., 2001, 11(12): 2974-2978.
[5] Hong Y N, Lam J W Y, Tang B Z. Aggregation-induced emission- phenomenon mechanism and applications[J]. Chem. Commun., 2009, (29): 4332-4353.
[6] Dong Y Q, Lam J W Y, Li Z, Qin A J, Tong H, Dong Y P, Feng X D, Tang B Z. Vapochromism of hexaphenylsilole[J]. J. Inorg. Organomet. Polym., 2005, 15(2): 287-291.
[7] Dong Y Q, Lam J W Y, Qin A J, Li Z, Sun J Z, Sung H H Y, Williams I D, Tang B Z. Switching the light emission of (4-biphenylyl)phenyldibenzofulvene by morphological modulation: crystallization-induced emission enhancement[J]. Chem. Commun., 2007, (1): 40-42.
[8] Wu C C, Lin Y T, Wong K T, Chen R T, Chien Y Y. Efficient organic blue-light-emitting devices with double confinement on terfluorenes with ambipolar carrier transport properties[J]. Adv. Mater., 2004, 16(1): 61-65.
[9] Li Z, Dong Y Q, Tang Y H, Huler M, Tong H, Dong Y P, Lam J W Y, Wong K S. Gao P, Williams I D, Kwok H S, Tang B, Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materias[J]. J. Phys. Chem. B, 2005, 109(20): 10061-10066.
[10] Sartin M M, Boydston A J, Pagenkopf B L, Bard A J. Electrochemistry, spectroscopy, and electrogenerated chemiluminescence of silole-based chromophores[J]. J. Am. Chem. Soc., 2006, 128(31): 10163-10170.
[11] Dong Y Q, Lam J W Y, Qin A J, Liu J Z, Li Z, Tang B Z. Aggregation-induced emissions of tetraphenylethene derivatives and their utilities as chemical vapor sensors and in organic light-emitting diodes[J]. Appl. Phys. Lett., 2007, 91(1): 11111-11113.
[12] Liu Y, Deng C M, Tang L, Qin A J, Hu R R, Sun J Z, Tang B Z. Specific detection of D-glucose by a tetraphenylethene-based fluorescent sensor[J]. J. Am. Chem. Soc., 2011, 133(4): 660-663.
[13] Liu L, Zhang G X, Xiang J F, Zhang D Q, Zhu D B. Fluorescence "Turn On" chemosensors for Ag⁺ and Hg²⁺ based on tetraphenylethylene motif featuring adenine and thymine moieties[J]. Org. Lett., 2008, 10(20): 4581-4584.
[14] 闫继明,秦安军,孙景志,唐本忠. 聚集诱导发光分子在生物检测领域的应用[J]. 科学通报,2010,55(13):1206-1213. Yan G M, Qin A J, Sun J Z, Tang B Z. Application of AIE-active molecules in biosening[J]. Chin. Sci. Bull., 2010, 55(13): 1206-1213.
[15] 张双,秦安军,孙景志,唐本忠. 聚集诱导发光机理研究[J]. 化学进展, 2011,23(4):623-636. Zhang S, Qin A J, Sun J Z, Tang B Z. Mechanism study of aggregation-induced emission[J]. Progress in Chemistry, 2011, 23(4): 623-636.
[16] 李振. 聚集诱导发光研究的新进展[J]. 科学通报,2010,55(23):2267-2268. Li Z. New progress in aggregation-induced emission research[J]. Chin. Sci. Bull., 2010, 55(23): 2267-2269.
[17] Wu J S, Liu W M, Ge J C, Zhang H Y, Wang P F. New sensing mechanisms for design of fluorescent chemosensors emerging in recent years[J]. Chem. Soc. Rev., 2011, 40(7): 3483-3495.
[18] Tong H, Hong Y N, Dong Y Q, Haussler M, Lam J W Y, Li Z, Guo Z F, Guo Z H, Tang B Z. Fluorescent "light-up" bioprobes based on tetraphenylethylene derivatives with aggregation-induced emission characteristics[J]. Chem. Commun., 2006, (35): 3705-3707.
[19] Tong H, Hong Y N, Dong Y Q, Haeussler M, Li Z, Lam J W Y, Dong Y P, Sung H H Y, Williams I D, Tang B Z. Protein detection and quantitation by tetraphenylethene-based fluorescent probes with aggregation-induced emission characteristics[J]. J. Phys. Chem. B, 2007, 111(40): 11817-11823.
[20] Park C, Hong J I. A new fluorescent sensor for the detection of pyrophosphate based on a tetraphenylethylene moiety[J]. Tetrahedron Lett., 2010, 51(15): 1960-1962.
[21] Shiraishi K, Sanji T, Tanaka M. A displacement assay for the sensing of protein interactions using sugar-tetraphenylethene conjugates[J]. Tetrahedron Lett., 2010, 51(48): 6331-6333.
[22] Chen Q, Bian N, Cao C, Qiu X L, Qi A D, Han B H, Glucosamine hydrochloride functionalized tetraphenylethylene: a novel fluorescent probe for alkaline phosphatase based on the aggregation-induced emissiom[J]. Chem. Commun., 2010, 46(23): 4067-4069.
[23] Wang J X, Chen Q, Bian N, Yang F, Sun J, Qi A D, Yan C G, Han B H. Sugar-bearing tetraphenylethylene: novel fluorescent probe for studies of carbohydrate-protein interaction based on aggregation-induced emission[J]. Org. Biomol. Chem., 2011, 9(7): 2219-2226.
[24] Kato T, Kawaguchi A, Nagata K, Hatanaka K. Development of tetraphenylethylene-based fluorescent oligosaccharide probes for detection of influenza virus[J]. Biochem. Biophys. Res. Commun., 2010, 394(1): 200-204.
[25] Liu Y, Yu Y, Lam J W Y, Hong Y N, Faisal M, Yuan W Z, Tang B Z. Simple biosensor with high selectivity and sensitivity: thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol-ene click mechanism[J]. Chem. Eur. J., 2010, 16(28): 8433-8438.
[26] Nakamura M, Sanji T, Tanaka M. Fluorometric sensing of biogenic amines with aggregation-induced emission-active tetraphenylethenes[J]. Chem. Eur. J., 2011, 17(19): 5344-5349.
[27] Liu Y, Chen S M, Lam J W Y, Lu P, Kwok R T K, Mahtab F, Kwok H S, Tang B Z. Tuning the electronic nature of aggregation-induced emission luminogens with enhanced hole-transporting property[J]. Chem. Mater., 2011, 23(10): 2536-2544.
[28] Zhao Z J, Li Z F, Lam J W Y, Maldonado J L, Ortia G R, Liu Y, Yuan W Z, Xu J B, Miao Q, Tang B Z. High hole mobility of 1,2-bis-1,2-diphenylethene in field effect transistor[J]. Chem. Commun., 2011, 47(24): 6924-6926.
[29] Zhao Z J, Chen S M, Lam J W Y, Wang Z M, Lu Pi, Mahtab F,. Sung H H, Williams I D, Ma Y, Kwok H S, Tang B Z. Pyrene-substituted ethenes: aggregation-enhanced excimer emission and highly efficient electroluminescence[J]. J. Mater. Chem., 2011, 21(20): 7210-7216.
[30] Luo X L, Li J N, Li C H, Heng L P, Dong Y Q, Liu Z P, Bo Z S, Tang B Z. Reversible switching of the emission of diphenyldibenzofulvenes by thermal and mechanical stimuli[J]. Adv. Mater., 2011, 23(29): 3261-3265.
[31] Li H Y, Chi Z G, Xu B J, Zhang X Q, Li X F, Liu S W, Zhang Y, Xu J R. Aggregation-induced emission enhancement compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties[J]. J. Mater. Chem., 2011, 21(11): 3760-3767.
[32] Zhang X Q, Chi Z G, Li H Y, Xu B G, Li X F, Liu S W, Zhang Y, Xu J R. Synthesis and properties of novel aggregation-induced emission compounds with combined tetraphenylethylene and dicarbazolyl triphenylethylene moieties[J]. J. Mater. Chem., 2011, 21(6): 1788-1796.
[33] Zhang X Q, Chi Z G, Li H Y, Xu B G, Li X F, Zhou W, Liu S W, Zhang Y, Xu J R. Piezofluorochromism of an Aggregation-Induced Emission Compound Derived from Tetraphenylethylene[J]. Chem. Asian J., 2011, 6(3): 808-811.
[34] Xu B J, Chi Z G, Zhang J Y, Zhang X Q, Li H Y, Li X F, Liu S W, Zhang Y, Xu J R. Piezofluorochromic and aggregation-induced-emission compounds containing triphenylethylene and tetraphenylethylene moieties[J]. Chem. Asian J., 2011, 6(6): 1470-1478.
[35] Wang W Z, Lin T T, Wang M, Liu T X, Ren L L, Chen D, Huang S. Aggregation emission properties of oligomers based on tetraphenylethylene[J]. J. Phys. Chem. B, 2010, 114(18): 5983-5988.
[36] Lu P, Lam J W Y, Liu J Z, Jim C K W, Yuan W Z, Xie N, Zhong Y C, Hu Q, Wong K S, Cheuk K K L, Tang B Z. Aggregation-induced emission in a hyperbranched poly(silylenevinylene) and superamplification in its emission quenching by explosives[J]. Macromol. Rapid Commun., 2010, 31(9-10): 834-839.
[37] Wang J, Mei J, Yuan W Z, Lu P, Qin A J, Sun J Z, Ma Y G, Tang B Z. Hyperbranched polytriazoles with high molecular compressibility: aggregation-induced emission and superamplified explosive detection[J]. J. Mater. Chem., 2011, 21(12): 4056-4059.
[38] Hu X M, Chen Q, Zhou D, Cao J, He Y J, Han B H. One-step preparation of fluorescent inorganic-organic hybrid material used for explosive sening[J]. Polym. Chem., 2011, 2(5): 1124-1128.