TY - JOUR

T1 - Imparting Stability to Organic Photovoltaic Components through Molecular Engineering

T2 - Mitigating Reactions with Singlet Oxygen

AU - Henke, Petr

AU - Rindom, Cecilie

AU - Kanta Aryal, Um

AU - Frydenlund Jespersen, Malte

AU - Broløs, Line

AU - Mansø, Mads

AU - Turkovic, Vida

AU - Madsen, Morten

AU - Mikkelsen, Kurt V.

AU - Ogilby, Peter R.

AU - Brøndsted Nielsen, Mogens

N1 - Funding Information: The Independent Research Fund Denmark, Technology and Production Sciences (0136‐00081B) and The Novo Nordisk Foundation (NNF20OC0061574) are acknowledged for financial support. Publisher Copyright: © 2023 The Authors. ChemSusChem published by Wiley-VCH GmbH.

PY - 2023

Y1 - 2023

N2 - One key challenge in the development of viable organic photovoltaic devices is to design component molecules that do not degrade during combined exposure to oxygen and light. Such molecules should thus remain comparatively unreactive towards singlet molecular oxygen and not act as photosensitizers for the generation of this undesirable species. Here, novel redox-active chromophores that combine these two properties are presented. By functionalizing indenofluorene-extended tetrathiafulvalenes (IF-TTFs) with cyano groups at the indenofluorene core using Pd-catalyzed cyanation reactions, we find that the reactivity of the exocyclic fulvene carbon-carbon double bonds towards singlet oxygen is considerably reduced. The new cyano-functionalized IF-TTFs were tested in non-fullerene acceptor based organic photovoltaic proof-of-principle devices, revealing enhanced device stability.

AB - One key challenge in the development of viable organic photovoltaic devices is to design component molecules that do not degrade during combined exposure to oxygen and light. Such molecules should thus remain comparatively unreactive towards singlet molecular oxygen and not act as photosensitizers for the generation of this undesirable species. Here, novel redox-active chromophores that combine these two properties are presented. By functionalizing indenofluorene-extended tetrathiafulvalenes (IF-TTFs) with cyano groups at the indenofluorene core using Pd-catalyzed cyanation reactions, we find that the reactivity of the exocyclic fulvene carbon-carbon double bonds towards singlet oxygen is considerably reduced. The new cyano-functionalized IF-TTFs were tested in non-fullerene acceptor based organic photovoltaic proof-of-principle devices, revealing enhanced device stability.

KW - Cross-coupling

KW - Fused-ring systems

KW - Heterocycles

KW - Photophysics

KW - Singlet oxygen

U2 - 10.1002/cssc.202202320

DO - 10.1002/cssc.202202320

M3 - Journal article

C2 - 36897647

AN - SCOPUS:85153405694

JO - ChemSusChem

JF - ChemSusChem

SN - 1864-5631

ER -