A Modular Cascade Synthetic Strategy Toward Structurally Constrained Boron-Doped Polycyclic Aromatic Hydrocarbons
Zhang JJ, Yang L, Liu F, Fu Y, Liu J, Popov AA, Ma J, Feng X (2021)
Publication Type: Journal article
Publication year: 2021
Journal
Book Volume: 60
Pages Range: 25695-25700
Journal Issue: 49
Abstract
A novel synthetic strategy was developed for the construction of difficult-to-access structurally constrained boron-doped polycyclic aromatic hydrocarbons (sc-B-PAHs) via a cascade reaction from the readily available ortho-aryl-substituted diarylalkynes. This domino process involves borylative cyclization, 1,4-boron migration and successive two-fold electrophilic borylation. Two types of sc-B-PAHs bearing B-doped [4]helicene (1 a-1 i) or BN-doped [4]helicene (1 n-1 t) and double [4]helicene (1 u-1 v) are constructed by this cascade reaction. Remarkably, this synthetic strategy is characterized by modest yields (20–50 %) and broad substrate scope (18 examples) with versatile functional group tolerance. The resultant sc-B-PAHs show good stability under ambient conditions and are thoroughly investigated by X-ray crystallography, UV/Vis absorption and fluorescence spectroscopy, and cyclic voltammetry. Interestingly enough, BN-doped [4]helicene 1 o forms a unique alternating π-stacked dimer of enantiomers within a helical columnar superstructure, while BN-doped double [4]helicene 1 u establishes an unprecedented π-stacked trimeric sandwich structure with a rare 2D lamellar π-stacking. The synthetic approach reported herein represents a powerful tool for the rapid generation of novel sc-B-PAHs, which are highly attractive for the elucidation of the structure-property relationship and for potential optoelectronic applications.
Involved external institutions
Technische Universität Dresden
Germany (DE)
Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden
Germany (DE)
University of Hong Kong (HKU) / 香港大學
Hong Kong (HK)
Germany (DE)
Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden
Germany (DE)
University of Hong Kong (HKU) / 香港大學
Hong Kong (HK)
How to cite
APA:
Zhang, J.-J., Yang, L., Liu, F., Fu, Y., Liu, J., Popov, A.A.,... Feng, X. (2021). A Modular Cascade Synthetic Strategy Toward Structurally Constrained Boron-Doped Polycyclic Aromatic Hydrocarbons. Angewandte Chemie International Edition, 60(49), 25695-25700. https://doi.org/10.1002/anie.202109840
MLA:
Zhang, Jin-Jiang, et al. "A Modular Cascade Synthetic Strategy Toward Structurally Constrained Boron-Doped Polycyclic Aromatic Hydrocarbons." Angewandte Chemie International Edition 60.49 (2021): 25695-25700.
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