Thieno[3,2-b]thiophene fused BODIPYs: synthesis, near-infrared luminescence and photosensitive properties
- 15 March 2019
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 17 (14), 3617-3622
- https://doi.org/10.1039/c9ob00030e
Abstract
The fusion of π-sufficient heteroaryl moieties has proven to be an effective strategy for achieving the red shift of the main spectral bands of BODIPY. In this paper, thieno[3,2-b]thiophene-fused BODIPY derivatives 1 and 2 have been designed and characterized by various spectroscopic methods, and their photosensitive properties have also been explored. Both dyes absorb in the near-infrared region with extremely high molar extinction coefficients, due to the extension of π-conjugation by fusion of the thieno[3,2-b]thiophene moiety. Their fluorescence quantum yields and singlet oxygen generation properties are significantly affected by iodine substitutions; dye 2 displays a moderate singlet oxygen generation value of 0.32, which makes it a potential NIR photosensitizer for photodynamic therapy of cancer in future research.Keywords
Funding Information
- National Natural Science Foundation of China (21801057, 21871072, 21501073, 21471042)
- Hangzhou Normal University
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