期刊
JOURNAL OF PHYSICAL CHEMISTRY C
卷 116, 期 19, 页码 10541-10547出版社
AMER CHEMICAL SOC
DOI: 10.1021/jp303100a
关键词
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资金
- National Science Foundation of China [21074113, 50873086]
- Ministry of Science and Technology of China [2009CB623605]
- Natural Science Foundation of Zhejiang Province [Z4110056]
- Research Grants Council of Hong Kong [603509, HKUST2/CRF/10, 604711]
- University Grants Committee of Hong Kong [AoE/P-03/08]
- Cao Guangbiao Foundation of Zhejiang University
By integrating N,N-dimethyl (donor, D) and fumaronitrile (acceptor, A) groups with the biphenyl fluorogen, which has an aggregation-induced emission (AIE) property, we have obtained the target molecule 2-(4-bromophenyl)-3-(4'-(dimethylamino)-biphenyl-4-yl) fumaronitrile (BDABFN). BDABFN is a red-to-near-infrared-emitting fluorogen with emission peaks at 653 and 710 nm for its amorphous and crystal solids, respectively. BDABFN shows an evident aggregation-induced emission property, and the fluorescence quantum efficiency of its solid is 26.5%. Cystallographic data indicate that there is no pi-pi stacking, and neither J- nor H-aggregates are observed between the adjacent molecules. The existence of multiple C-H center dot center dot center dot pi bonds between the adjacent molecules restricts the intramolecular rotation of the D and A moieties and enables the fluorogen to emit intensely in the solid states. Meanwhile, because of strong intramolecular D-A interaction, BDABFN exhibits pronounced solvatochromism, and the fluorescence peak red-shifts from 552 nm in hexane (nonpolar and hydrophobic solvent) to 750 nm in tetrahydrofuran (polar and hydrophilic solvent. BDABFN also displays a typical twisted intramolecular charge transfer property in polar solvents because of the interaction between the N,N-dimethyl and fumaronitrile moieties.
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