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Title: Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs

Abstract

In this work, a selective stepwise annulation of indigo has been demonstrated as a means of providing both monoannulated and differentially double-annulated indigo derivatives. Disparate substitution of the electron accepting bay-annulated indigo system allows for fine control over both the electronic properties as well as donor-acceptor structural architectures. Optical and electronic properties were characterized computationally as well as through UV-vis absorption spectroscopy and cyclic voltammetry. Finally, this straightforward method provides a modular approach for the design of indigo-based materials with tailored optoelectronic properties.

Authors:
 [1];  [2];  [2]
  1. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry; Univ. of California, Berkeley, CA (United States). Department of Chemistry
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry
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:
1437951
Grant/Contract Number:  
[AC02-05CH11231]
Resource Type:
Accepted Manuscript
Journal Name:
Organic Letters
Additional Journal Information:
[ Journal Volume: 18; Journal Issue: 20; Related Information: © 2016 American Chemical Society.]; Journal ID: ISSN 1523-7060
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Kolaczkowski, Matthew A., He, Bo, and Liu, Yi. Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs. United States: N. p., 2016. Web. doi:10.1021/acs.orglett.6b02504.
Kolaczkowski, Matthew A., He, Bo, & Liu, Yi. Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs. United States. doi:10.1021/acs.orglett.6b02504.
Kolaczkowski, Matthew A., He, Bo, and Liu, Yi. Mon . "Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs". United States. doi:10.1021/acs.orglett.6b02504. https://www.osti.gov/servlets/purl/1437951.
@article{osti_1437951,
title = {Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs},
author = {Kolaczkowski, Matthew A. and He, Bo and Liu, Yi},
abstractNote = {In this work, a selective stepwise annulation of indigo has been demonstrated as a means of providing both monoannulated and differentially double-annulated indigo derivatives. Disparate substitution of the electron accepting bay-annulated indigo system allows for fine control over both the electronic properties as well as donor-acceptor structural architectures. Optical and electronic properties were characterized computationally as well as through UV-vis absorption spectroscopy and cyclic voltammetry. Finally, this straightforward method provides a modular approach for the design of indigo-based materials with tailored optoelectronic properties.},
doi = {10.1021/acs.orglett.6b02504},
journal = {Organic Letters},
number = [20],
volume = [18],
place = {United States},
year = {2016},
month = {10}
}

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Free Publicly Available Full Text
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Cited by: 11 works
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