Synthesis and Semiconducting Characteristics of the BF2 Complexes of Bisbenzothiophene-Fused Azadipyrromethenes

A novel type of dibenzothiophene [b]-fused core-expanded azaBODIPYs were obtained through an efficient post-functionalization of tetrabrominated azadipyrromethenes, using CuI-catalyzed cyclization, followed by BF2 complexation. These dyes show nearly planar skeletons, strong NIR absorption with maxi...

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Bibliographic Details
Published in:Organic letters 2020-01, Vol.22 (1), p.185-189
Main Authors: Sheng, Wanle, Chang, Fei, Wu, Qinghua, Hao, Erhong, Jiao, Lijuan, Wang, Jie-Yu, Pei, Jian
Format: Article
Language:English
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Summary:A novel type of dibenzothiophene [b]-fused core-expanded azaBODIPYs were obtained through an efficient post-functionalization of tetrabrominated azadipyrromethenes, using CuI-catalyzed cyclization, followed by BF2 complexation. These dyes show nearly planar skeletons, strong NIR absorption with maximum peaks up to 733 nm, and remarkable low-lying LUMO level of −4.15 eV. The field-effect transistor based on 1b exhibits bipolar transport properties, with the highest electron and hole mobilities up to 0.012 and 0.046 cm2 V–1 s–1, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04142