TY - JOUR
T1 - Regioselectively α- And β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties
AU - Shimada, Takahide
AU - Mori, Shigeki
AU - Ishida, Masatoshi
AU - Furuta, Hiroyuki
N1 - Funding Information:
The present work was supported by JSPS KAKENHI Grant Numbers (JP19H04586 and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged.
Publisher Copyright:
© 2020 Shimada et al.
PY - 2020/4/1
Y1 - 2020/4/1
N2 - A series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S0–S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.
AB - A series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S0–S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.
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U2 - 10.3762/bjoc.16.53
DO - 10.3762/bjoc.16.53
M3 - Article
AN - SCOPUS:85084400736
VL - 16
SP - 587
EP - 595
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -