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Solid-state absorption, luminescence, and singlet fission of furanyl-substituted diketopyrrolopyrroles with different pi-stacking arrangements
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SYSNO ASEP 0579769 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Solid-state absorption, luminescence, and singlet fission of furanyl-substituted diketopyrrolopyrroles with different pi-stacking arrangements Author(s) Kratochvíl, M. (CZ)
Thottappali, Muhammed Arshad (UMCH-V) RID, ORCID
Luňák, S. Jr. (CZ)
Pauk, K. (CZ)
Rais, David (UMCH-V) RID
Marková, A. (CZ)
Pfleger, Jiří (UMCH-V) RID, ORCID
Imramovský, A. (CZ)
Vala, M. (CZ)Article number e202300201 Source Title ChemPhotoChem . - : Wiley - ISSN 2367-0932
Roč. 7, č. 12 (2023)Number of pages 9 s. Language eng - English Country US - United States Keywords singlet fission ; diketopyrrolopyrrole ; solid state photophysics OECD category Materials engineering R&D Projects GA22-02005S GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support UMCH-V - RVO:61389013 UT WOS 001082536700001 EID SCOPUS 85173874070 DOI https://doi.org/10.1002/cptc.202300201 Annotation Small modifications of the diketopyrrolopyrrole (DPP) molecular structure induced remarkable changes in its spectral and photophysical behavior. Using furan (F) heterosubstitution instead of thiophene (T) substituent resulted in a small blue shift and decreased Huang-Rhys factor of the absorption spectra in solution, irrespectively to N,N'-alkyls. Branching of alkyl side chains by formal 2-ethylation of n-hexyl substituent (C6 to EH) switched the slipped-stack arrangement, irrespectively on the heteroatoms. Consequent changes in steady-state absorption spectra of thin films were interpreted using time dependent density functional theory calculations, carried out on model dimers. Solid-state luminescence is weak and partially dependent on an excitation wavelength. Singlet fission was observed by femtosecond transient absorption spectroscopy, with considerably different yields for variously π-stacked FDPP-EH (30 %) and FDPP-C6 (160 %). The shape of triplet-triplet absorption spectra was also influenced by various π-stacking. The results are discussed in terms of different mixing of both Frenkel and charge transfer states in model dimers and different excitonic and electronic coupling in both types of π-stacks, visualized by natural transition orbitals. Workplace Institute of Macromolecular Chemistry Contact Eva Čechová, cechova@imc.cas.cz ; Tel.: 296 809 358 Year of Publishing 2025 Electronic address https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202300201
Number of the records: 1