Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 40, Pages 21817-21823Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202106490
Keywords
aromaticity; DFT calculations; luminescence; main-group elements; reaction mechanisms
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Funding
- JSPS KAKENHI from MEXT [JP20H05868, JP20H05869]
- Swedish Research Council [2019-05618, 2016-07213]
- JSPS KAKENHI [JP19K22165, JP20H02722]
- Research Program of Five-star Alliance in NJRC Mater. Dev.
- Swedish Research Council [2019-05618] Funding Source: Swedish Research Council
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This study presents experimental and theoretical investigations on the ground- and excited-state antiaromaticity/aromaticity as well as the photophysical properties of an isolable 1,3,2,4-diazadiboretidine derivative. The compound exhibits different geometrical configurations and characteristics in various states, as revealed by experimental and theoretical calculations.
1,3,2,4-Diazadiboretidine, an isoelectronic heteroanalogue of cyclobutadiene, is an interesting chemical species in terms of comparison with the carbon system, whereas its properties have never been investigated experimentally. According to Baird's rule, Huckel antiaromatic cyclobutadiene acquires aromaticity in the lowest triplet state. Here we report experimental and theoretical studies on the ground- and excited-state antiaromaticity/aromaticity as well as the photophysical properties of an isolable 1,3,2,4-diazadiboretidine derivative. The crystal structure of the diazadiboretidine derivative revealed that the B2N2 ring adopts a planar rhombic geometry in the ground state. Yet, theoretical calculations showed that the B2N2 ring turns to a square geometry with a nonaromatic character in the lowest triplet state. Notably, the diazadiboretidine derivative has the lowest singlet and triplet states lying at close energy levels and displays blue phosphorescence.
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