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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)
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: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. doi: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 = {2016},
month = {10}
}

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Cited by: 11 works
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Works referencing / citing this record:

High-Performance Ambipolar Polymers Based on Electron-Withdrawing Group Substituted Bay-Annulated Indigo
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Deep‐Red Lasing and Amplified Spontaneous Emission from Nature Inspired Bay‐Annulated Indigo Derivatives
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  • Shukla, Atul; Wallwork, Nicholle R.; Li, Xin
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Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red-Emitting Dyes with Conformational Freedom
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  • Sadowski, Bartłomiej; Rode, Michał F.; Gryko, Daniel T.
  • Chemistry - A European Journal, Vol. 24, Issue 4
  • DOI: 10.1002/chem.201702306

Functional Organic Semiconductors Based on Bay‐Annulated Indigo (BAI)
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Design and effective synthesis methods for high-performance polymer semiconductors in organic field-effect transistors
journal, January 2017

  • Shi, Longxian; Guo, Yunlong; Hu, Wenping
  • Materials Chemistry Frontiers, Vol. 1, Issue 12
  • DOI: 10.1039/c7qm00169j

Isatin and its derivatives: a survey of recent syntheses, reactions, and applications
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  • Varun, Varun; Sonam, Sonam; Kakkar, Rita
  • MedChemComm, Vol. 10, Issue 3
  • DOI: 10.1039/c8md00585k

Near-infrared organic photodetectors based on bay-annulated indigo showing broadband absorption and high detectivities up to 1.1 μm
journal, January 2018

  • Verstraeten, Frederik; Gielen, Sam; Verstappen, Pieter
  • Journal of Materials Chemistry C, Vol. 6, Issue 43
  • DOI: 10.1039/c8tc04164d

Discovery and properties of a new indigoid structure type based on dimeric cis -indigos
journal, January 2020

  • Hong, Hyejin; Conover, Cassidy M.; Hofsommer, Dillon T.
  • Organic & Biomolecular Chemistry, Vol. 18, Issue 30
  • DOI: 10.1039/d0ob01368d

Synthesis and Properties of a Bay-Annulated-Indigo Tetramer Based on Low-Cost Spiro[Fluorene-9,9′-Xanthene] Core
journal, October 2019