Towards meso-Ester BODIPYs with Aggregation-Induced Emission Properties: The Effect of Substitution Positions

• Published in: Chemistry, an Asian journal Vol. 10; no. 8; pp. 1631 - 1634
• Main Authors: Chua, Ming Hui, Ni, Yong, Garai, Monalisa, Zheng, Bin, Huang, Kuo-Wei, Xu, Qing-Hua, Xu, Jianwei, Wu, Jishan
• Format: Journal Article
• Language: English
• Published: Germany Blackwell Publishing Ltd 01.08.2015; Wiley Subscription Services, Inc
• Subjects: aggregation-induced emission; bodipy; Chemistry; fluorescence; near-infrared; organic dyes; aggregation-induced emission; organic dyes; near-infrared; fluorescence; bodipy
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201500420

Three meso‐ester boron dipyrromethene (BODIPY) dyes have been synthesized and functionalized with aggregation‐induced emission (AIE)‐active tetraphenylethene or triphenylethene moieties. It was found that functionalizing at the different positions of the BODIPY core resulted in the final dye having different emission properties in response to aggregation: from aggregation‐induced quenching (ACQ) to being AIE active. X‐ray crystallographic analysis was thus performed to provide an explanation for these differences. AIE AIE Captain: Attachment of AIE‐active groups to an ACQ luminogen does not always lead to AIE properties. Herein, we have synthesized three meso‐ester BODIPY dyes, each with an AIE‐active triphenylethene or tetraphenylethene moiety functionalized at different positions of the core, thus providing derivatives that are ACQ, mildly ACQ, or AIE‐active.