Engineering the Photophysics of Cyanines by Chain C1′ Substituents

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F25%3A00143252" target="_blank" >RIV/00216224:14310/25:00143252 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22340/25:43932902

Výsledek na webu

<a href="https://pubs.acs.org/doi/10.1021/acs.joc.5c02283" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.joc.5c02283</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.5c02283" target="_blank" >10.1021/acs.joc.5c02283</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Engineering the Photophysics of Cyanines by Chain C1′ Substituents

Popis výsledku v původním jazyce

Cyanine dyes are widely used in bioimaging, sensing, optoelectronic, and medicinal applications due to their tunable photophysical properties. However, controlling their electronic structures and photophysical properties remains a challenge. Here we report a general synthetic route to pentamethine and heptamethine cyanines bearing C1 ' chain substituents that allow substantial control of their electronic, photophysical, and photochemical properties. By varying the terminal heterocycle and introducing various substituents at the 1 '-position, we investigated the role of symmetry breaking and its impact on bond length alternation (BLA) and out-of-plane rotation (OPR). Our analysis shows that OPR, coupled with BLA, suppresses or hypsochromically shifts the first absorption band, thereby significantly altering the absorption properties of the studied dyes. This effect is particularly pronounced in structures with different heterocyclic end groups and bulky or electron deficient substituents at the 1 '-position. Through quantum chemical calculations and spectroscopic analyses, we demonstrate how these modifications can be used to tune optical properties of these dyes across the visible region, paving the way for their further customization.

Název v anglickém jazyce

Engineering the Photophysics of Cyanines by Chain C1′ Substituents

Popis výsledku anglicky

Cyanine dyes are widely used in bioimaging, sensing, optoelectronic, and medicinal applications due to their tunable photophysical properties. However, controlling their electronic structures and photophysical properties remains a challenge. Here we report a general synthetic route to pentamethine and heptamethine cyanines bearing C1 ' chain substituents that allow substantial control of their electronic, photophysical, and photochemical properties. By varying the terminal heterocycle and introducing various substituents at the 1 '-position, we investigated the role of symmetry breaking and its impact on bond length alternation (BLA) and out-of-plane rotation (OPR). Our analysis shows that OPR, coupled with BLA, suppresses or hypsochromically shifts the first absorption band, thereby significantly altering the absorption properties of the studied dyes. This effect is particularly pronounced in structures with different heterocyclic end groups and bulky or electron deficient substituents at the 1 '-position. Through quantum chemical calculations and spectroscopic analyses, we demonstrate how these modifications can be used to tune optical properties of these dyes across the visible region, paving the way for their further customization.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

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

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

—

Svazek periodika

90

Číslo periodika v rámci svazku

50

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

17

Strana od-do

17797-17813

Kód UT WoS článku

001632706100001

EID výsledku v databázi Scopus

—