Dithienylthiazolothiazole with B ← N Bond toward Electron-Deficient BN Embedded Polycyclic Heteraromatic Molecule
A novel chemically stable boron-nitrogen (BN) embedded dithienylthiazolothiazole unit was synthesized, namely <b>BNTz</b>, with mesitylene group linked to the four-coordinate boron atom. The B ← N bond is crucial in facilitating a rigid and coplanar conformation, reducing the LUMO energy level. Consequently, the <b>BNTz</b> unit demonstrates significant electron mobility (8.14 × 10<sup>-4</sup> cm<sup>2</sup> V<sup>-1</sup> s<sup>-1</sup>), possesses low LUMO energy levels (-3.73 eV), and shows strong absorbance within the visible spectrum. A thorough examination of the electrochemical and photophysical characteristics, along with theoretical analyses, was conducted. It was observed that fluorescence quenching occurs between PBDB-T and the <b>BNTz</b>, suggesting effective exciton dissociation. <b>BNTz</b> holds potential for further development in constructing novel n-type semiconductors.
Authors
- Lingpeng Yan (ORCID: https://orcid.org/0000-0003-1177-8558)
- Tongtong Dang (ORCID: https://orcid.org/0009-0004-7777-8264)
- Tao Li (ORCID: https://orcid.org/0000-0002-2410-0175)
- Jiabin Zhang (ORCID: https://orcid.org/0000-0001-6400-077X)
- Yan Feng
Institutions
- Shanghai Jiao Tong University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Laboratoire de Synthèse Organique (FR)
- Chemical Synthesis Lab (SG)
- Taiyuan University of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-25
- DOI
- https://doi.org/10.1021/acs.joc.5c01535
- Primary Topic
- Organic Electronics and Photovoltaics
- Type
- article
- Field-Weighted Citation Impact
- 0.00