Synthesis and Spectroscopic Properties of Selenophene[3, 2‑b]‑Fused BODIPYs

Fusion selenophene endows the chromophore with more intrinsic and special functions. Herein, nonsymmetric selenophene-fused BODIPYs were designed and synthesized starting from the selenophene unit. The fused ring of selenophene not only maintains the rigid structure of BODIPY but also further modula...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 9; pp. 5291 - 5299
Main Authors Di, Linting, Gai, Lizhi, Wen, Chengyong, Hu, Siyi, Feng, Jiao, Sui, Xinbing, Lu, Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.05.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DYES
PHOTODYNAMIC THERAPY
DERIVATIVES
PHOTOSENSITIZERS
PROBES
Online AccessGet full text

Cover

More Information
Summary:Fusion selenophene endows the chromophore with more intrinsic and special functions. Herein, nonsymmetric selenophene-fused BODIPYs were designed and synthesized starting from the selenophene unit. The fused ring of selenophene not only maintains the rigid structure of BODIPY but also further modulates its spectral properties. The newly prepared dyes possessed many promising properties including large molar extinction coefficients, low fluorescence quantum yields, and moderate singlet oxygen generation. Quantum calculations affirmed that the smaller singlet-triplet energy gap and larger spin–orbit coupling cause efficient intersystem crossing, thus enhancing the singlet oxygen generation yield. Furthermore, selenophene-fused BODIPY exhibited significant phototoxicity with negligible dark cytotoxicity, based on the fluorescence imaging of the reactive oxygen species detection experiment.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02604