Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2-b]pyrroles

Author:

Poronik Yevgen M.,Baryshnikov Glib V.ORCID,Deperasińska Irena,Espinoza Eli M.ORCID,Clark John A.,Ågren HansORCID,Gryko Daniel T.ORCID,Vullev Valentine I.ORCID

Abstract

AbstractElectron-deficient π-conjugated functional dyes lie at the heart of organic optoelectronics. Adding nitro groups to aromatic compounds usually quenches their fluorescence via inter-system crossing (ISC) or internal conversion (IC). While strong electronic coupling of the nitro groups with the dyes ensures the benefits from these electron-withdrawing substituents, it also leads to fluorescence quenching. Here, we demonstrate how such electronic coupling affects the photophysics of acceptor–donor–acceptor fluorescent dyes, with nitrophenyl acceptors and a pyrrolo[3,2-b]pyrrole donor. The position of the nitro groups and the donor-acceptor distance strongly affect the fluorescence properties of the bis-nitrotetraphenylpyrrolopyrroles. Concurrently, increasing solvent polarity quenches the emission that recovers upon solidifying the media. Intramolecular charge transfer (CT) and molecular dynamics, therefore, govern the fluorescence of these nitro-aromatics. While balanced donor-acceptor coupling ensures fast radiative deactivation and slow ISC essential for large fluorescence quantum yields, vibronic borrowing accounts for medium dependent IC via back CT. These mechanistic paradigms set important design principles for molecular photonics and electronics.

Funder

Stiftelsen Olle Engkvist Byggmästare

Fundacja na rzecz Nauki Polskiej

National Research Foundation of Korea

National Science Foundation

Publisher

Springer Science and Business Media LLC

Subject

Materials Chemistry,Biochemistry,Environmental Chemistry,General Chemistry

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