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  A modular cascade synthetic strategy toward structurally constrained boron-doped polycyclic aromatic hydrocarbons

Zhang, J.-J., Yang, L., Liu, F., Fu, Y., Liu, J., Popov, A. A., et al. (2021). A modular cascade synthetic strategy toward structurally constrained boron-doped polycyclic aromatic hydrocarbons. Angewandte Chemie International Edition, 60(49), 25695-25700. doi:10.1002/anie.202109840.

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Angewandte Chemie Intl Edit - 2021 - Zhang - A Modular Cascade Synthetic Strategy Toward Structurally Constrained.pdf (Publisher version), 3MB
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Angewandte Chemie Intl Edit - 2021 - Zhang - A Modular Cascade Synthetic Strategy Toward Structurally Constrained.pdf
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2021
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https://doi.org/10.1002/anie.202109840 (Publisher version)
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 Creators:
Zhang, Jin-Jiang1, Author
Yang, Lin1, Author
Liu, Fupin1, Author
Fu, Yubin1, Author
Liu, Junzhi1, Author
Popov, Alexey A.1, Author
Ma, Ji1, Author
Feng, Xinliang2, Author              
Affiliations:
1External Organizations, ou_persistent22              
2Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society, ou_3316580              

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Free keywords: BORYLATIVE CYCLIZATION; COLUMNAR ORGANIZATION; NANOGRAPHENES; SYSTEMS; PAHSChemistry; boron doping; helicenes; polycyclic aromatic hydrocarbons; structure constraint; supramolecular behavior;
 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 pi-stacked dimer of enantiomers within a helical columnar superstructure, while BN-doped double [4]helicene 1 u establishes an unprecedented pi-stacked trimeric sandwich structure with a rare 2D lamellar pi-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.

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Language(s): eng - English
 Dates: 2021-10-082021-12-01
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: ISI: 000714783700001
DOI: 10.1002/anie.202109840
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (49) Sequence Number: - Start / End Page: 25695 - 25700 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851