Electronic structure and spectroscopic properties of (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines and their model oligomers

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F15%3APU111659" target="_blank" >RIV/00216305:26310/15:PU111659 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.synthmet.2014.11.035" target="_blank" >http://dx.doi.org/10.1016/j.synthmet.2014.11.035</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.synthmet.2014.11.035" target="_blank" >10.1016/j.synthmet.2014.11.035</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Electronic structure and spectroscopic properties of (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines and their model oligomers

Popis výsledku v původním jazyce

The synthesis, chemical and spectroscopic characterization of four novel (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines containing pyridine (DPPn2), pyrrole (DPPy2), thiophene (DPTh2) and furan (DPFu2) units were presented. The experimental absorption spectra in methanol exhibit very broad lowest energy band with the maximum ranged from 307 nm for DPFu2 to 443 nm for DPPn2. The most intense fluorescence was observed for the molecules containing the pyrrole heterocycles in dichloromethane. The role of the (2S,3S)-2,3-diphenyl-2,3-dihydropyrazine as the spectroscopic or electrochemical active central building block was also estimated theoretically for the series of symmetric V-shaped model molecules containing two hexamer oligomers. In this context, the quantum chemical calculations were used for the investigation of the molecular electronic structure, ionisation potentials, electron affinities and molecular orbital energy diagrams of neutral and charged states. The calculations of the B3LYP-D(COSMO) pair-interaction energies for two model clusters of DPPy2(CH3OH)2 and DPPy2(CH2Cl2)2 indicated the possible formation of the hydrogen bonds between the solvent molecules and nitrogen atoms of central 2,3-dihydropyrazine and pyrrole units.

Název v anglickém jazyce

Electronic structure and spectroscopic properties of (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines and their model oligomers

Popis výsledku anglicky

The synthesis, chemical and spectroscopic characterization of four novel (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines containing pyridine (DPPn2), pyrrole (DPPy2), thiophene (DPTh2) and furan (DPFu2) units were presented. The experimental absorption spectra in methanol exhibit very broad lowest energy band with the maximum ranged from 307 nm for DPFu2 to 443 nm for DPPn2. The most intense fluorescence was observed for the molecules containing the pyrrole heterocycles in dichloromethane. The role of the (2S,3S)-2,3-diphenyl-2,3-dihydropyrazine as the spectroscopic or electrochemical active central building block was also estimated theoretically for the series of symmetric V-shaped model molecules containing two hexamer oligomers. In this context, the quantum chemical calculations were used for the investigation of the molecular electronic structure, ionisation potentials, electron affinities and molecular orbital energy diagrams of neutral and charged states. The calculations of the B3LYP-D(COSMO) pair-interaction energies for two model clusters of DPPy2(CH3OH)2 and DPPy2(CH2Cl2)2 indicated the possible formation of the hydrogen bonds between the solvent molecules and nitrogen atoms of central 2,3-dihydropyrazine and pyrrole units.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1211" target="_blank" >LO1211: Centrum materiálového výzkumu na FCH VUT v Brně - udržitelnost a rozvoj</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Syntetic Metals

ISSN

0379-6779

e-ISSN

—

Svazek periodika

2015

Číslo periodika v rámci svazku

199

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

10

Strana od-do

319-328

Kód UT WoS článku

000348954000045

EID výsledku v databázi Scopus

2-s2.0-84917706140