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Design and synthesis of benzothiadiazole-based molecular systems: self-assembly, optical and electronic properties
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SYSNO ASEP 0554827 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Design and synthesis of benzothiadiazole-based molecular systems: self-assembly, optical and electronic properties Author(s) Miranda-Olvera, M. (MX)
Arcos-Ramos, R. (MX)
Maldonado-Domínguez, Mauricio (UFCH-W) ORCID
Salmon, L. (FR)
Molnar, G. (FR)
Bousseksou, A. (FR)
del Pilar Carreon-Castro, M. (MX)Source Title New Journal of Chemistry. - : Royal Society of Chemistry - ISSN 1144-0546
Roč. 46, č. 11 (2022), s. 4992-5001Number of pages 10 s. Language eng - English Country GB - United Kingdom Keywords field-effect transistors ; solar-cells ; fluorescent ; ionization ; dyes ; semiconductors ; derivatives ; emission ; polymers ; affinity Subject RIV CF - Physical ; Theoretical Chemistry OECD category Physical chemistry Research Infrastructure e-INFRA CZ - 90140 - CESNET, zájmové sdružení právnických osob Method of publishing Limited access Institutional support UFCH-W - RVO:61388955 UT WOS 000754547000001 EID SCOPUS 85127364309 DOI 10.1039/d1nj04559h Annotation A set of small benzothiadiazole (BTD)-based derivatives with a D-A-D architecture were synthesized and characterized as building blocks of organic semiconducting materials by applying an experimental-theoretical approach. The four derivatives tend to self-assemble into highly ordered crystalline solids, with varying degrees of responsiveness to mechanical and thermal stimuli. The featured derivatives exhibit absorption maxima in solution and molar extinction coefficient values related to pi-pi* electronic transitions with minor solvatochromic responses, displaying broad fluorescence profiles with large Stokes shifts and high fluorescence quantum yields. In the solid-state, the BTD derivatives display absorption maxima in the visible range and intense fluorescence emission of the n-butoxy and fluorene derivatives. The stability of the one-electron reduced and oxidized forms of all compounds was assessed by means of cyclic voltammetry, which complemented by DFT calculations allowed the identification of one BTD derivative (BuO-BTD) as a strong candidate for use as an electron transport layer in organoelectronic devices. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2023 Electronic address http://hdl.handle.net/11104/0329464
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