Citation: Peng Zhe, Ji Yingchun, Wang Zhi, Tong Bin, Shi Jianbing, Dong Yuping. Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior[J]. Acta Chimica Sinica, ;2016, 74(11): 942-948. doi: 10.6023/A16080406 shu

Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior

1.
School of Materials Science and Engineering, Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, Beijing Institute of Technology, Beijing 100081

Corresponding author: Tong Bin, tongbin@bit.edu.cn Dong Yuping, chdongyp@bit.edu.cn
Received Date: 13 August 2016

Fund Project: National Natural Science Foundation of China 51328302National Natural Science Foundation of China 21474009National Basic Research Program of China 973 Program: 2013CB834704

Figures(8)

A new A-D-A type pyrrolopyrrole-based derivative 4', 4"-(2, 5-diphenyl-pyrrolo[3, 2-b]pyrrole-1, 4-diyl) bis ([1, 1'-biphenyl]-4-carbonitrile) (DPPDC) was synthesized via Suzuki coupling reaction between 1, 4-bis (4-bromophenyl)-2, 5-diphenyl-1, 4-dihydropyrrolo[3, 2-b]pyrrole and 4-cyanophenylboronic acid. The fluorescent emission intensities of DPPDC in pure THF solution and lower fraction of water (φ_H2O≤60%) mixtures were weak at around 550 nm. When φ_H2O was 99% in THF/H₂O mixtures, the emission was enhanced and blue-shifted at around 505 nm. The maximal fluorescent emission intensity of DPPDC was 11 times higher than that of in pure THF solution, indicating DPPDC exhibiting AIE property. It was also found that four different kinds of crystal structures of DPPDC was cultivated from CHCl₂-Hexane, CHCl₃-Hexane and CHCl₃/Acetone-Hexane systems via solvent slow diffusion method. Four crystals respec-tively emitted blue, azure, green and turquoise at 467, 483, 496 and 493 nm, which manifested the polymorphism-dependent fluorescent emission property of DPPDC. Additionally, trifluoroacetic acid (TFA) could make the emitting color change from yellow to orange-red with as-prepared paper containing DPPDC due to the acid-base interaction. The obvious emitting color change of DPPDC can be used as a visual sensor to detect acid gas.
- polymorphism,
- pyrrolopyrrole,
- acid response,
- aggregation-induced emission
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