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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/00216275:25310/23:39920680

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

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

Popis výsledku anglicky

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

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA19-22783S" target="_blank" >GA19-22783S: Molekulární materiály pro získávání energie: směrem k překročení limitů</a><br>

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

ChemPhotoChem

ISSN

2367-0932

e-ISSN

—

Svazek periodika

e202300201

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

„“-„“

Kód UT WoS článku

001082536700001

EID výsledku v databázi Scopus

2-s2.0-85173874070