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
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
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
Original language description
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.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/8J24AT022" target="_blank" >8J24AT022: Side chain engineering of adamantane for highly ordered organic semiconductor pigments and dyes</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic & biomolecular chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Volume of the periodical
28
Issue of the periodical within the volume
23
Country of publishing house
GB - UNITED KINGDOM
Number of pages
21
Pages from-to
6718-6737
UT code for WoS article
001509820600001
EID of the result in the Scopus database
—