Tuning NIR Absorption and Emission of Diphenyl-Dihydrophenazine-Based Merocyanines with Ultra Narrow Band Gap

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F26%3A0200447" target="_blank" >RIV/00216305:26310/26:0200447 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216275:25310/25:39923169

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202501864" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202501864</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.202501864" target="_blank" >10.1002/chem.202501864</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Tuning NIR Absorption and Emission of Diphenyl-Dihydrophenazine-Based Merocyanines with Ultra Narrow Band Gap

Popis výsledku v původním jazyce

Five merocyanine derivatives with a 5,10-diphenyl-dihydrophenazine donor and various indanone-and indandione based-acceptors with one or two dicyanovinylene groups were prepared by Knoevenagel condensation for tuning absorption and fluorescence in the near-infrared region. Molecular conformation, bond length alternation, and molecular packing in the solid state were studied by X-ray diffraction of single crystals in combination with density functional theory (DFT) calculations. By enhancing electron-accepting ability, a considerable decrease of lowest unoccupied molecular orbitals (LUMO) energy by 1.01 eV and retained highest occupied molecular orbitals (HOMO) energy within 0.13 eV were estimated by cyclic and rotating disc electrode voltammetry, relating semi-quantitatively to DFT prediction. Optical properties in solutions with various polarity, neat amorphous films, and crystalline powder states were studied. The absorption maxima of the neat films evolved from 545 nm to 931 nm. An ultranarrow optical band gap of DPPZ-IDD (1.09 eV) was found from the onset of thin film absorption and well agreed with the electrochemical gap of 0.93 eV. Detectable fluorescence in the NIR region was observed in the film and polycrystalline powder states.

Název v anglickém jazyce

Tuning NIR Absorption and Emission of Diphenyl-Dihydrophenazine-Based Merocyanines with Ultra Narrow Band Gap

Popis výsledku anglicky

Five merocyanine derivatives with a 5,10-diphenyl-dihydrophenazine donor and various indanone-and indandione based-acceptors with one or two dicyanovinylene groups were prepared by Knoevenagel condensation for tuning absorption and fluorescence in the near-infrared region. Molecular conformation, bond length alternation, and molecular packing in the solid state were studied by X-ray diffraction of single crystals in combination with density functional theory (DFT) calculations. By enhancing electron-accepting ability, a considerable decrease of lowest unoccupied molecular orbitals (LUMO) energy by 1.01 eV and retained highest occupied molecular orbitals (HOMO) energy within 0.13 eV were estimated by cyclic and rotating disc electrode voltammetry, relating semi-quantitatively to DFT prediction. Optical properties in solutions with various polarity, neat amorphous films, and crystalline powder states were studied. The absorption maxima of the neat films evolved from 545 nm to 931 nm. An ultranarrow optical band gap of DPPZ-IDD (1.09 eV) was found from the onset of thin film absorption and well agreed with the electrochemical gap of 0.93 eV. Detectable fluorescence in the NIR region was observed in the film and polycrystalline powder states.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10400 - Chemical sciences

Projekt

<a href="/cs/project/GA24-10479S" target="_blank" >GA24-10479S: Molekulární krystaly s blízkou infračervenou emisí pro zobrazování nové generace (Crystal-NIR)</a><br>

Návaznosti

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

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Chemistry

ISSN

0947-6539

e-ISSN

1521-3765

Svazek periodika

31

Číslo periodika v rámci svazku

42

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

16

Strana od-do

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Kód UT WoS článku

001524476700001

EID výsledku v databázi Scopus

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