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Updated: Feb 11, 2026
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
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B-Heterocyclic Carbene Arising from Charge Shift: A Computational Verification
Congjie Zhang1, Fan Fan1, Zhimin Wang1
1Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 2, 2018
Summary
Researchers designed novel compounds derived from 1-Borabicyclo[1.1.0]but-2(3)-ene (1BB) that exhibit carbene and ligand properties. These compounds enable the creation of unique structures with planar tetracoordinate carbon and boron.
Area of Science:
- Computational Chemistry
- Organometallic Chemistry
- Materials Science
Background:
- 1-Borabicyclo[1.1.0]but-2(3)-ene (1BB) is a singlet biradical with potential for ionic resonance.
- The ionic resonance structure of 1BB can function as a B-heterocyclic carbene (BHC), exhibiting carbene, Lewis base, and ligand behavior.
Purpose of the Study:
- To design and investigate novel stable compounds derived from 1BB.
- To explore the reactivity and coordination chemistry of these compounds as carbenes and ligands.
- To develop a new strategy for synthesizing compounds featuring planar tetracoordinate carbon (ptC) and boron (ptB).
Main Methods:
- Employed a range of quantum chemical methods for theoretical design and analysis.
- Investigated the structures, stability, and Wiberg bond indices of Lewis adducts and metal complexes.
- Studied reactions with various Lewis acids (e.g., BePh2, BH3, AlH3, AlCl3) and transition metals (Cu, Ag, Au).
Main Results:
- Successfully designed four types of stable compounds (A-D) retaining 1BB's unique characteristics.
- Compounds A-D demonstrated reactivity as carbenes and functioned as L- and Z-type ligands.
- Formation of complexes with planar tetracoordinate carbon (ptC) and planar tetracoordinate boron (ptB) was achieved.
- Binuclear complexes containing both ptC and ptB were also synthesized.
Conclusions:
- A novel and rational method for designing compounds with ptC and ptB has been established.
- The designed compounds integrate carbene, ptC, ptB, and ligand functionalities.
- These compounds are anticipated to be valuable for future experimental synthesis and applications in chemistry.
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