Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F13%3A00394402" target="_blank" >RIV/61389013:_____/13:00394402 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1021/jp4033832" target="_blank" >http://dx.doi.org/10.1021/jp4033832</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jp4033832" target="_blank" >10.1021/jp4033832</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties

Popis výsledku v původním jazyce

Unsubstituted 2,5-bis(2,2-bithiophene-5-yl)-1,3,4-thiadiazole and four of its derivatives containing solubilizing octyl groups in different positions of the terminal thiophene ring were synthesized. Their UV?vis absorption and emission spectra turned outto be strongly dependent on the position of the substituent and showed significant bathochromic shifts of the dominant transition for compounds with the substituents attached to C? of the terminal ring. A good correlation was found for the experimentally determined and theoretically calculated excitation energies employing the TD CAM-B3LYP functional. The calculations showed, in addition, that the alkyl substituents improved the planarity of the molecule and its aromaticity, and that they raised the HOMO and LUMO levels via electron-donating effects. The only exception was the compound with the substituent attached to the inner C? position. In this case, the absorption band originating from the dominant transition was hypsochromically

Název v anglickém jazyce

Semiconducting alkyl derivatives of 2,5-bis(2,2'-bithiophene-5-yl)-1,3,4-thiadiazole-effect of the substituent position on the spectroscopic, electrochemical, and structural properties

Popis výsledku anglicky

Unsubstituted 2,5-bis(2,2-bithiophene-5-yl)-1,3,4-thiadiazole and four of its derivatives containing solubilizing octyl groups in different positions of the terminal thiophene ring were synthesized. Their UV?vis absorption and emission spectra turned outto be strongly dependent on the position of the substituent and showed significant bathochromic shifts of the dominant transition for compounds with the substituents attached to C? of the terminal ring. A good correlation was found for the experimentally determined and theoretically calculated excitation energies employing the TD CAM-B3LYP functional. The calculations showed, in addition, that the alkyl substituents improved the planarity of the molecule and its aromaticity, and that they raised the HOMO and LUMO levels via electron-donating effects. The only exception was the compound with the substituent attached to the inner C? position. In this case, the absorption band originating from the dominant transition was hypsochromically

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

BM - Fyzika pevných látek a magnetismus

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Physical Chemistry C

ISSN

1932-7447

e-ISSN

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Svazek periodika

117

Číslo periodika v rámci svazku

29

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

15316-15326

Kód UT WoS článku

000322503600050

EID výsledku v databázi Scopus

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