Nonsymmetric Benzo[a]fused and Thiophene/Thieno[3,2-b]thiophene[b]fused BODIPYs: Synthesis and Photophysical Properties

被引:19
作者
Di, Linting [1 ,2 ]
Yang, Jie [1 ,2 ]
Tang, Weiguo [1 ,2 ]
Gai, Lizhi [1 ,2 ,3 ]
Zhou, Zhikuan [1 ,2 ]
Lu, Hua [1 ,2 ]
机构
[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Peoples R China
[2] Hangzhou Normal Univ, Key Lab Organosilicon Mat Technol Zhejiang Prov, Hangzhou 311121, Peoples R China
[3] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Nanjing 210093, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORESCENCE-SPECTRA; FACILE SYNTHESIS; DYES; FUNCTIONALIZATION; DERIVATIVES; DESIGN; SCALE; EDGE;
D O I
10.1021/acs.joc.0c02274
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The fusion of sufficient-electron heterocycle rings into the[a]/[b]-position of the BODIPY core would result in a large redshift wavelength, thus achieving red or near infrared emission. In this paper, we described the synthesis of nonsymmetric benzo[a]fused and thiophene/thieno[3,2-b]thiophene[b]fused BODIPY derivatives 2-3 while containing a reactive site, and then, 4-7 were developed by nucleophilic substitution reactions of 3 with various nucleophilic agents in high yields. X-ray crystallographic analysis of 2-7 revealed that the core structure adopted a planar geometry and pi-pi interactions were observed in the packing structure. BODIPYs 4 and 6-7 displayed a hypochromic shift in the absorption and bathochromic shift in the emission with increasing solvent polarity because of the formation of resonance structures resulting from the change of the C-N distance, which was rationalized by density functional theory (DFT)/time-dependent-DFT calculations.
引用
收藏
页码:601 / 608
页数:8
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