The Synergistic Effect between Triphenylpyrrole Isomers as Donors, Linking Groups, and Acceptors on the Fluorescence Properties of D–π–A Compounds in the Solid State

• Published in: Chemistry : a European journal Vol. 24; no. 2; pp. 434 - 442
• Main Authors: Lei, Yunxiang, Lai, Yueyin, Dong, Lichao, Shang, Guojun, Cai, Zhengxu, Shi, Jianbing, Zhi, Junge, Li, Pengfei, Huang, Xiaobo, Tong, Bin, Dong, Yuping
• Format: Journal Article
• Language: English
• Published: Germany 09.01.2018
• Subjects: aggregation induced emission; donor–pi–acceptor systems; piezochromic properties; triphenylpyrrole isomer donors; piezochromic properties; triphenylpyrrole isomer donors; aggregation induced emission; donor-pi-acceptor systems
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201704020

Eight donor–π–acceptor (D–π–A) compounds employing triphenylpyrrole isomers (TPP‐1,2,5 and TPP‐1,3,4) as donors, malononitrile (CN) and 1H‐indene‐1,3(2H)‐dione (CO) as acceptors, pyridone (P) and benzopyran (B) as π‐linking groups were synthesized. The compounds exhibited aggregation‐induced emission and piezochromic properties. Compared with previously reported donors, triphenylpyrroles induced all the compounds to have more remarkable photophysical properties. The compounds containing TPP‐1,2,5 and P moieties displayed stronger fluorescence intensities, shorter emission wavelengths, and more distinct piezochromic properties. However, the same phenomenon was observed in the TPP‐1,3,4‐containing system if B was as π‐linker. Moreover, the CN acceptor endowed the compound to have a relatively strong fluorescent intensity, in which CO induced a relatively long emission wavelength. That is, the photophysical properties of D–π–A compounds can be controlled by adjusting the structure of donor, linker and acceptor. A harmonious triangle: The eight donor–π–acceptor (D–π–A)compounds employing triphenylpyrrole isomers as donors, malononitrile (CN) and 1H‐indene‐1,3(2H)‐dione (CO) as acceptors, and pyridone (P) and benzopyran (B) as π‐linking groups exhibit aggregation‐induced emission (AIE) properties and evident piezochromic properties. The synergistic effect between donors, linking groups, and acceptors on the fluorescence properties in the solid state may be clearly observed