Similar and Different: Effect of Substitution Pattern on the Aggregation-Induced Emission Property of [4'-(bisphenylamino)[1,1']biphenyl]methylene Fluorenes

Abstract:

Three isomers, [4'-(bisphenylamino)[1,1']biphen-2-yl]methylenefluorene (BAB2MF), [4'-(bisphenylamino)[1,1']biphen-3-yl]methylenefluorene (BAB3MF) and [4'-(bisphenylamino)[1,1']biphen-4-yl]methylenefluorene (BAB4MF), were synthesized through Suzuki coupling. The substitution pattern exerts a dramatic influence on the optical property. BAB3MF and BAB4MF are hardly emissive either in the solution or as solid state. On the contrary, BAB2MF emits strongly, especially in the aggregate state with a high fluorescent quantum yield of 69%. Furthermore, BAB2MF shows an aggregation-induced enhanced emission behavior. BAB2MF solid emits at 488 nm, about 60 nm blue-shifted from its solution.

• Periodical: Advanced Materials Research (Volume 859)
• Pages: 329-332
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.859.329
• Online since: December 2013
• Authors: Zhi Chen, Yi Long Xie, Jin Xing Qiu, Zhong He Chen*
• Keywords: Aggregation Induced Enhanced Emission , Fluorene, Substitution Pattern, Triphenylamine

References

[1] Y.N. Hong, J.W. Y, Lam B.Z. Tang. Aggregation-induced emission. Chem. Soc. Rev. Vol. 40(2011), p.5361.

[2] G.F. Zhang, M.P. Aldred, W.L. Gong, C. Li, M.Q. Zhu. Utilising tetraphenylethene as a dual activator for intramolecular charge transfer and aggregation induced emission. Chem. Commun. Vol. 48 (2012), p.7711.

DOI: 10.1039/c2cc33218c

[3] H.C. Yeh, S.J. Yeh, C.T. Chen. Readily synthesized arylamino fumaronitrile for non-doped red organic light-emitting diodes. Chem. Commun. Vol. 20 (2003) , p.2632.

DOI: 10.1039/b309780c

[4] Z.Y. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, M. Kakimoto. Spin-coated highly efficient phosphorescent organic light-emitting diodes based on bipolar triphenylamine-benzimidazole derivatives. Adv. Funct. Mater. Vol. 18(2008).

DOI: 10.1002/adfm.200700913

[5] H.J. Yen, C.J. Chen, G.S. Liou. Novel high-efficiency PL polyimide nanofiber containing aggregation-induced emission (AIE)-active cyanotriphenylamine luminogen. Chem. Commun. Vol. 49(2013), p.630.

DOI: 10.1039/c2cc37857d

[6] Wang BB, Qian Y. Synthesis and efficient solid-state emission of conjugated donor-acceptor-donor triphenylamine chromophores. New. J. Chem. Vol. 37(2013), p.1402.

DOI: 10.1039/c3nj41115j

[7] Y.Q. Dong, J.W.Y. Lam, A.J. Qin, Z. Li, J.Z. Sun, H.H.Y. Sung, I.D. Williams, B.Z. Tang. Switching the light emission of (4-biphenylyl)phenyldibenzofulvene by morphological modulation: crystallization-induced emission enhancement. Chem. Commun. Vol. 1(2007).

DOI: 10.1039/b613157c

[8] Y.X. Li, Z. Chen, Cui Y, Xia GM, Yang XF. Substitution position directing the molecular packing, electronic structure, and aggregate emission property of bis[2-(9-anthracenyl)vinyl]benzene system. J Phys. Chem. C. Vol. 116(2012), p.6401.

DOI: 10.1021/jp211364m

[9] T.L. Fletcher, M.J. Namkung, J. R Dice, Schaefer SK. Derivatives of fluorene. XIX. 9-ο-chlorocinnamylidenefluorene and related compounds. J. Med. Chem. Vol. 8(1965), p.347.

DOI: 10.1021/jm00327a014

[10] Papalambros L, Nikokavouras J. Benzylidenefluorene ozonolysis under chemiluminescence mimetic conditions in homogeneous and micellar media. I. Kinetic law as a function of Hammett's σ constants and quenching by the leaving moiety. J. Photochem. Vol. 39(1987).

DOI: 10.1016/0047-2670(87)80008-4

[11] Gupta KC, Srivastava N, Nigam RK. Efect of bulky size of carbonyl systems on betaine decomposition of semistabilized arsonium ylids. Ind .J. Chem. B. Vol. 20B(1981) , pp.802-803.

[12] A. Winter, C. Friebe, M.D. Hager, U.S. Schubert. Synthesis of rigid π-conjugated mono-, bis-, tris-, and tetrakis(terpyridine)s: influence of the degree and pattern of substitution on the photophysical properties. Eur. J. Org. Chem. Vol. 2009(2009).

DOI: 10.1002/ejoc.200800857

[13] C.W. Lee, J.A. Seo, M.S. Gong, J.Y. Lee. The effect of the substitution position of dibenzofuran on the photophysical and charge-transport properties of host materials for phosphorescent organic light-emitting diodes. Chem. Eur. J. Vol. 19(2013).

DOI: 10.1002/chem.201203778

[14] Z.J. Zhao, S.M. Chen, J.W.Y. Lam, Z.M. Wang, P. Lu, F. Mahtab , H.H.Y. Sung, I.D. Williams, Y.G. Ma, H.S. Kwok, B.Z. Tang. Pyrene-substituted ethenes: aggregation-enhanced excimer emission and highly efficient electroluminescence. J. Mater. Chem. Vol. 21(2011).

DOI: 10.1039/c0jm04449k

[15] Y.X. Li, H.B. Zhou, J.L. Miao G.X. Sun, G.B. Li, Y. Nie, C.L. Chen, Z. Chen, X.T. Tao. Conformation twisting induced orientational disorder, polymorphism and solid-state emission properties of 1-(9-anthryl)-2-(1-naphthyl)ethylene. CrystEngComm. Vol. 14(2012).

DOI: 10.1039/c2ce26098k