Electron-Deficient Polycyclic π-System Fused with Multiple B→N Coordinate Bonds

Yirui Cao; Congzhi Zhu; Maciej Barłóg; Kayla P. Barker; Xiaozhou Ji; Alexander J. Kalin; Mohammed Al-Hashimi; Lei Fang

doi:10.1021/acs.joc.0c02052

Electron-Deficient Polycyclic π-System Fused with Multiple B→N Coordinate Bonds

Yirui Cao, Congzhi Zhu^*, Maciej Barłóg, Kayla P. Barker, Xiaozhou Ji, Alexander J. Kalin, Mohammed Al-Hashimi^*, Lei Fang^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

An extensive polycyclic π-system with 23 fused rings is synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B→N coordinate bonds are formed in one pot. B→N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and organic photovoltaics.

Original language	English
Pages (from-to)	2100-2106
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	86
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.0c02052
Publication status	Published - 5 Feb 2021
Externally published	Yes

Access to Document

10.1021/acs.joc.0c02052

Cite this

@article{5d60ec18338149cd8e8a58f08dc4c437,

title = "Electron-Deficient Polycyclic π-System Fused with Multiple B→N Coordinate Bonds",

abstract = "An extensive polycyclic π-system with 23 fused rings is synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B→N coordinate bonds are formed in one pot. B→N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and organic photovoltaics.",

author = "Yirui Cao and Congzhi Zhu and Maciej Bar{\l}{\'o}g and Barker, \{Kayla P.\} and Xiaozhou Ji and Kalin, \{Alexander J.\} and Mohammed Al-Hashimi and Lei Fang",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = feb,

day = "5",

doi = "10.1021/acs.joc.0c02052",

language = "English",

volume = "86",

pages = "2100--2106",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Electron-Deficient Polycyclic π-System Fused with Multiple B→N Coordinate Bonds

AU - Cao, Yirui

AU - Zhu, Congzhi

AU - Barłóg, Maciej

AU - Barker, Kayla P.

AU - Ji, Xiaozhou

AU - Kalin, Alexander J.

AU - Al-Hashimi, Mohammed

AU - Fang, Lei

PY - 2021/2/5

Y1 - 2021/2/5

N2 - An extensive polycyclic π-system with 23 fused rings is synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B→N coordinate bonds are formed in one pot. B→N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and organic photovoltaics.

AB - An extensive polycyclic π-system with 23 fused rings is synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B→N coordinate bonds are formed in one pot. B→N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and organic photovoltaics.

UR - https://www.scopus.com/pages/publications/85100219952

U2 - 10.1021/acs.joc.0c02052

DO - 10.1021/acs.joc.0c02052

M3 - Article

AN - SCOPUS:85100219952

SN - 0022-3263

VL - 86

SP - 2100

EP - 2106

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Electron-Deficient Polycyclic π-System Fused with Multiple B→N Coordinate Bonds

Abstract

Access to Document

Other files and links

Fingerprint

Cite this