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Title: Low Band Gap Coplanar Conjugated Molecules Featuring Dynamic Intramolecular Lewis Acid–Base Coordination

Abstract

Ladder-type conjugated molecules with a low band gap and low LUMO level were synthesized through an N-directed borylation reaction of pyrazine-derived donor-acceptor-donor precursors. The intramolecular boron-nitrogen coordination bonds played a key role in rendering the rigid and coplanar conformation of these molecules and their corresponding electronic structures. Experimental investigation and theoretical simulation revealed the dynamic nature of such coordination, which allowed for active manipulation of the optical properties of these molecules by using competing Lewis basic solvents.

Authors:
 [1];  [1];  [1];  [2];  [1];  [1]
  1. Texas A & M Univ., College Station, TX (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1530241
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Organic Chemistry
Additional Journal Information:
Journal Volume: 81; Journal Issue: 10; Journal ID: ISSN 0022-3263
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Zhu, Congzhi, Guo, Zi-Hao, Mu, Anthony U., Liu, Yi, Wheeler, Steven E., and Fang, Lei. Low Band Gap Coplanar Conjugated Molecules Featuring Dynamic Intramolecular Lewis Acid–Base Coordination. United States: N. p., 2016. Web. doi:10.1021/acs.joc.6b00238.
Zhu, Congzhi, Guo, Zi-Hao, Mu, Anthony U., Liu, Yi, Wheeler, Steven E., & Fang, Lei. Low Band Gap Coplanar Conjugated Molecules Featuring Dynamic Intramolecular Lewis Acid–Base Coordination. United States. doi:10.1021/acs.joc.6b00238.
Zhu, Congzhi, Guo, Zi-Hao, Mu, Anthony U., Liu, Yi, Wheeler, Steven E., and Fang, Lei. Wed . "Low Band Gap Coplanar Conjugated Molecules Featuring Dynamic Intramolecular Lewis Acid–Base Coordination". United States. doi:10.1021/acs.joc.6b00238. https://www.osti.gov/servlets/purl/1530241.
@article{osti_1530241,
title = {Low Band Gap Coplanar Conjugated Molecules Featuring Dynamic Intramolecular Lewis Acid–Base Coordination},
author = {Zhu, Congzhi and Guo, Zi-Hao and Mu, Anthony U. and Liu, Yi and Wheeler, Steven E. and Fang, Lei},
abstractNote = {Ladder-type conjugated molecules with a low band gap and low LUMO level were synthesized through an N-directed borylation reaction of pyrazine-derived donor-acceptor-donor precursors. The intramolecular boron-nitrogen coordination bonds played a key role in rendering the rigid and coplanar conformation of these molecules and their corresponding electronic structures. Experimental investigation and theoretical simulation revealed the dynamic nature of such coordination, which allowed for active manipulation of the optical properties of these molecules by using competing Lewis basic solvents.},
doi = {10.1021/acs.joc.6b00238},
journal = {Journal of Organic Chemistry},
number = 10,
volume = 81,
place = {United States},
year = {2016},
month = {4}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 35 works
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