D-A-D compounds combining dithienopyrrole donors and acceptors of increasing electron-withdrawing capability: synthesis, spectroscopy, electropolymerization, and electrochromism
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F22%3A00558515" target="_blank" >RIV/61389013:_____/22:00558515 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acs.jpcb.2c01772" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.jpcb.2c01772</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.jpcb.2c01772" target="_blank" >10.1021/acs.jpcb.2c01772</a>
Alternative languages
Result language
angličtina
Original language name
D-A-D compounds combining dithienopyrrole donors and acceptors of increasing electron-withdrawing capability: synthesis, spectroscopy, electropolymerization, and electrochromism
Original language description
Five D-π-A-π-D compounds consisting of the same donor unit (dithieno[3,2-b:2′,3′-d]pyrrole, DTP), the same π-linker (2,5-thienylene), and different acceptors of increasing electron-withdrawing ability (1,3,4-thiadiazole (TD), benzo[c][1,2,5]thiadiazole (BTD), 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DPP), 1,2,4,5-tetrazine (TZ), and benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (NDI)) were synthesized. DTP-TD, DTP-BTD, and DTP-DPP turned out to be interesting luminophores emitting either yellow (DTP-TD) or near-infrared (DTP-BTD and DTP-DPP) radiation in dichloromethane solutions. The emission bands were increasingly bathochromically shifted with increasing solvent polarity. Electrochemically determined electron affinities (|EA|s) were found to be strongly dependent on the nature of the acceptor changing from 2.86 to 3.84 eV for DTP-TD and DTP-NDI, respectively, while the ionization potential (IP) values varied only weakly. Experimental findings were strongly supported by theoretical calculations, which correctly predicted the observed solvent dependence of the emission spectra. Similarly, the calculated IP and EA values were in excellent agreement with the experiment. DTP-TD, DTP-BTD, DTP-TZ, and DTP-NDI could be electropolymerized to yield polymers of very narrow electrochemical band gap and characterized by redox states differing in color coordinates and lightness. Poly(DTP-NDI) and poly(DTP-TD) showed promising electrochromic behavior, not only providing a rich color palette in the visible but also exhibiting near-infrared (NIR) electrochromism.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10404 - Polymer science
Result continuities
Project
<a href="/en/project/GA22-02005S" target="_blank" >GA22-02005S: Exciton transformation in supramolecular polymers for energy conversion</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Physical Chemistry B
ISSN
1520-6106
e-ISSN
1520-5207
Volume of the periodical
126
Issue of the periodical within the volume
22
Country of publishing house
US - UNITED STATES
Number of pages
17
Pages from-to
4089-4105
UT code for WoS article
000810687600001
EID of the result in the Scopus database
2-s2.0-85131737972