Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F23%3A00577178" target="_blank" >RIV/61388955:_____/23:00577178 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/23:43928511

Výsledek na webu

<a href="https://hdl.handle.net/11104/0346400" target="_blank" >https://hdl.handle.net/11104/0346400</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2023.143073" target="_blank" >10.1016/j.electacta.2023.143073</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations

Popis výsledku v původním jazyce

lambda 3-1H-Phosphole is a unique heterocyclic compound characterized by low aromaticity with a limited number of cross-coupling reactions to allow side-chain modification. This severely limits the use of pentasubstituted phospholes in materials chemistry, including organic light-emitting diodes (OLEDs), organic solar cells (OSCs) or probes. Therefore, we developed a procedure for simple side-chain modification by Suzuki reactions. The syn-thesized pentasubstituted phospholes with a pi-conjugated arm in position 2 of the phosphole ring were inves-tigated electrochemically. In addition to the electrochemical study, we measured also the UV-VIS and fluorescence spectra for the prepared 1H-phospholes. The experimentally acquired data were correlated with quantum chemical calculations. The oxidation and reduction of all derivatives in acetonitrile at various elec-trodes is (quasi)reversible, the respective potentials as well as the extent of intramolecular electron communi-cation and pi-delocalization depend on the combination of electron withdrawing and donating substituents. The difference between the first oxidation and the first reduction potential (Delta E1) can be correlated with excitation energy.

Název v anglickém jazyce

Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations

Popis výsledku anglicky

lambda 3-1H-Phosphole is a unique heterocyclic compound characterized by low aromaticity with a limited number of cross-coupling reactions to allow side-chain modification. This severely limits the use of pentasubstituted phospholes in materials chemistry, including organic light-emitting diodes (OLEDs), organic solar cells (OSCs) or probes. Therefore, we developed a procedure for simple side-chain modification by Suzuki reactions. The syn-thesized pentasubstituted phospholes with a pi-conjugated arm in position 2 of the phosphole ring were inves-tigated electrochemically. In addition to the electrochemical study, we measured also the UV-VIS and fluorescence spectra for the prepared 1H-phospholes. The experimentally acquired data were correlated with quantum chemical calculations. The oxidation and reduction of all derivatives in acetonitrile at various elec-trodes is (quasi)reversible, the respective potentials as well as the extent of intramolecular electron communi-cation and pi-delocalization depend on the combination of electron withdrawing and donating substituents. The difference between the first oxidation and the first reduction potential (Delta E1) can be correlated with excitation energy.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)

Projekt

<a href="/cs/project/GA18-12150S" target="_blank" >GA18-12150S: Syntéza a charakterizace polovodivých supramolekul nového typu a jejich použití pro přípravu organických tranzistorů (OFET)</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Electrochimica acta

ISSN

0013-4686

e-ISSN

1873-3859

Svazek periodika

468

Číslo periodika v rámci svazku

NOV 2023

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

143073

Kód UT WoS článku

001080793400001

EID výsledku v databázi Scopus

2-s2.0-85170424902