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

Ming Hui Chua; Yong Ni; Monalisa Garai; Bin Zheng; Kuo-Wei Huang; Qing-Hua Xu; Jianwei Xu; Jishan Wu

doi:10.1002/asia.201500420

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

Chem Asian J. 2015 Aug;10(8):1631-4. doi: 10.1002/asia.201500420. Epub 2015 Jun 17.

Authors

Ming Hui Chua^{1

2}, Yong Ni², Monalisa Garai², Bin Zheng³, Kuo-Wei Huang³, Qing-Hua Xu², Jianwei Xu⁴, Jishan Wu^{5

6}

Affiliations

¹ Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore, Singapore.
² Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.
³ KAUST Catalysis Center and Division of Physical Sciences&Engineering, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia.
⁴ Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore, Singapore. jw-xu@imre.a-star.edu.sg.
⁵ Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore, Singapore. chmwuj@nus.edu.sg.
⁶ Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore. chmwuj@nus.edu.sg.

PMID: 26043727
DOI: 10.1002/asia.201500420

Abstract

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.

Keywords: aggregation-induced emission; bodipy; fluorescence; near-infrared; organic dyes.