Electronic Tuning of Mixed Quinoidal-Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main-Chains

Anderson, Christopher L.; Dai, Nan; Teat, Simon J.; He, Bo; Wang, Shu; Liu, Yi

doi:10.1002/anie.201908609

Electronic Tuning of Mixed Quinoidal-Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main-Chains

Journal Article · Mon Oct 07 00:00:00 EDT 2019 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201908609· OSTI ID:1581610

^[1]; Dai, Nan ^[2]; Teat, Simon J. ^[3]; He, Bo ^[3]; Wang, Shu ^[2]; ^[3]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
Chinese Academy of Sciences, Beijing (China)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

The synthesis of conjugated polymers with ionic substituents directly bound to their main chain repeat units is a strategy for generating strongly electron-accepting conjugated polyelectrolytes, as demonstrated through the synthesis of a series of ionic azaquinodimethane (iAQM) compounds. The introduction of cationic substituents onto the quinoidal para-azaquinodimethane (AQM) core gives rise to a strongly electron-accepting building block, which can be employed in the synthesis of ionic small molecules and conjugated polyelectrolytes (CPEs). Electrochemical measurements alongside theoretical calculations indicate notably low-lying LUMO values for the iAQMs. The optical band gaps measured for these compounds are highly tunable based on structure, ranging from 2.30 eV in small molecules down to 1.22 eV in polymers. Here, the iAQM small molecules and CPEs showcase the band gap reduction effects of combining the donor-acceptor strategy with the bond-length alternation reduction strategy. As a demonstration of their utility, the iAQM CPEs so generated were used as active agents in photothermal therapy.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1581610

Alternate ID(s):: OSTI ID: 1576804

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 50 Vol. 58; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction Anderson, Christopher L.; Liang, Jiatao; Teat, Simon J. Chemical Communications, Vol. 56, Issue 32 https://doi.org/10.1039/d0cc00916d	journal	January 2020

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CCDC 2359138: Experimental Crystal Structure Determination L., Anderson, Christopher; Nan, Dai,; J., Teat, Simon https://doi.org/10.5517/ccdc.csd.cc2k5w7w The current record is supplemented by this dataset	dataset	January 2024
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Electronic Tuning of Mixed Quinoidal-Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main-Chains

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