Solid-State Absorption, Luminescence, and Singlet Fission of Furanyl-Substituted Diketopyrrolopyrroles with Different π-Stacking Arrangements

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F23%3APU149310" target="_blank" >RIV/00216305:26310/23:PU149310 - isvavai.cz</a>

Alternative codes found

RIV/00216275:25310/23:39920680

Result on the web

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202300201" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202300201</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cptc.202300201" target="_blank" >10.1002/cptc.202300201</a>

Result language

angličtina

Original language name

Solid-State Absorption, Luminescence, and Singlet Fission of Furanyl-Substituted Diketopyrrolopyrroles with Different π-Stacking Arrangements

Original language description

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 pi-stacked FDPP-EH (30 %) and FDPP-C6 (160 %). The shape of triplet-triplet absorption spectra was also influenced by various pi-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 pi-stacks, visualized by natural transition orbitals. Furanyl-substituted diketopyrrolopyrroles (DPP) with different branching of the alkyl side chains were studied. Both formed two distinct types of pi-stacking leading to H-aggregates with considerably different energetics in terms of mixed lowest Frenkel and charge transfer (CT) states. The combined effect of the molecular structure and solid-state arrangement lead to fast and efficient CT mediated singlet fission, with one of the highest efficiencies (160 %) ever reported within the DPP family.image

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

<a href="/en/project/GA19-22783S" target="_blank" >GA19-22783S: Molecular energy harvesting materials: towards breaking the limits</a><br>

Continuities

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

Publication year

2023

Confidentiality

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

Name of the periodical

ChemPhotoChem

ISSN

2367-0932

e-ISSN

—

Volume of the periodical

e202300201

Issue of the periodical within the volume

October

Country of publishing house

DE - GERMANY

Number of pages

10

Pages from-to

„“-„“

UT code for WoS article

001082536700001

EID of the result in the Scopus database

2-s2.0-85173874070