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:
-
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry; Univ. of California, Berkeley, CA (United States). Department of Chemistry
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- 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. https://doi.org/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. https://doi.org/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 = {Mon Oct 10 00:00:00 EDT 2016},
month = {Mon Oct 10 00:00:00 EDT 2016}
}
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Works referencing / citing this record:
Synthesis and Properties of a Bay-Annulated-Indigo Tetramer Based on Low-Cost Spiro[Fluorene-9,9′-Xanthene] Core
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