Chiral diketopyrrolo[3,4-c]pyrrole dyes with different substitution symmetry: impact of adamantyl groups on the photo-physical properties in solution and thin films

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F26%3A0198357" target="_blank" >RIV/00216305:26310/26:0198357 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00782h" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00782h</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d5ob00782h" target="_blank" >10.1039/d5ob00782h</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral diketopyrrolo[3,4-c]pyrrole dyes with different substitution symmetry: impact of adamantyl groups on the photo-physical properties in solution and thin films

Popis výsledku v původním jazyce

Here we propose a comparative study on four chiral 1,4-diketo-3,6-dithienylpyrrolo[3,4-c]pyrrole (DPP) dyes with different substitution symmetry on the lactam moieties: (i) symmetrically N-substituted dyes 1-2, bearing two (S)-beta-citronellyl (DPP-CT) or (S)-2-methylbutyl (DPP-MT) chains; (ii) non-symmetrically N-substituted dyes 3-4, where an adamantylmethyl appendage replaced one of the (S)-beta-citronellyl (DPP-ACT) or (S)-2-methylbutyl (DPP-AMT) chains. The four molecules were synthesized and subjected to detailed investigation of their photo-physical properties in solution (absorbance, fluorescence, cyclic voltammetry) and thin films (absorbance, electronic circular dichroism, optical microscopy), evaluating the impact of different chiral moieties (citronellyl vs. 2-methylbutyl chains) and of different substitution patterns exerted by the adamantane moiety (symmetrical vs. non-symmetrical DPPs). Special emphasis was given to the chiroptical study of thin films, discussing the origin of different supramolecular arrangements in the solid state. Putting together experimental and computational results, we rationalize the chiroptical behavior of these systems in comparison with that of other classes of DPP dyes recently investigated by our group.

Název v anglickém jazyce

Chiral diketopyrrolo[3,4-c]pyrrole dyes with different substitution symmetry: impact of adamantyl groups on the photo-physical properties in solution and thin films

Popis výsledku anglicky

Here we propose a comparative study on four chiral 1,4-diketo-3,6-dithienylpyrrolo[3,4-c]pyrrole (DPP) dyes with different substitution symmetry on the lactam moieties: (i) symmetrically N-substituted dyes 1-2, bearing two (S)-beta-citronellyl (DPP-CT) or (S)-2-methylbutyl (DPP-MT) chains; (ii) non-symmetrically N-substituted dyes 3-4, where an adamantylmethyl appendage replaced one of the (S)-beta-citronellyl (DPP-ACT) or (S)-2-methylbutyl (DPP-AMT) chains. The four molecules were synthesized and subjected to detailed investigation of their photo-physical properties in solution (absorbance, fluorescence, cyclic voltammetry) and thin films (absorbance, electronic circular dichroism, optical microscopy), evaluating the impact of different chiral moieties (citronellyl vs. 2-methylbutyl chains) and of different substitution patterns exerted by the adamantane moiety (symmetrical vs. non-symmetrical DPPs). Special emphasis was given to the chiroptical study of thin films, discussing the origin of different supramolecular arrangements in the solid state. Putting together experimental and computational results, we rationalize the chiroptical behavior of these systems in comparison with that of other classes of DPP dyes recently investigated by our group.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/8J24AT022" target="_blank" >8J24AT022: Inženýrství bočního řetězce adamantanu pro vysoce uspořádané organické polovodivé pigmenty a barviva</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

Organic & biomolecular chemistry

ISSN

1477-0520

e-ISSN

1477-0539

Svazek periodika

28

Číslo periodika v rámci svazku

23

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

21

Strana od-do

6718-6737

Kód UT WoS článku

001509820600001

EID výsledku v databázi Scopus

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