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

Journal Article · Mon Oct 10 00:00:00 EDT 2016 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.6b02504· OSTI ID:1437951

Kolaczkowski, Matthew A. ^[1]; He, Bo ^[2]; Liu, Yi ^[2]

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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

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.

• Research Organization: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
• Sponsoring Organization: USDOE Office of Science (SC), Basic Energy Sciences (BES)
• Grant/Contract Number: AC02-05CH11231
• OSTI ID: 1437951
• Journal Information: Organic Letters, Vol. 18, Issue 20; Related Information: © 2016 American Chemical Society.; ISSN 1523-7060
• Publisher: American Chemical Society
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY