High-Performance Near-Infrared Chlorinated Rylenecarboximide Fluorophores via Consecutive C-N and C-C Bond Formation

Ze-Hua Wu; Artem Skabeev; Yulian Zagranyarski; Ruomeng Duan; Jun-O Jin; Minseok Kwak; Thomas Basché; Klaus Müllen; Chen Li

doi:10.1002/anie.202315156

High-Performance Near-Infrared Chlorinated Rylenecarboximide Fluorophores via Consecutive C-N and C-C Bond Formation

Angew Chem Int Ed Engl. 2023 Dec 21;62(52):e202315156. doi: 10.1002/anie.202315156. Epub 2023 Nov 23.

Authors

Ze-Hua Wu^{1

2}, Artem Skabeev¹, Yulian Zagranyarski³, Ruomeng Duan⁴, Jun-O Jin⁵, Minseok Kwak⁶, Thomas Basché², Klaus Müllen^{1

2}, Chen Li^{1

4}

Affiliations

¹ Max-Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
² Department of Chemistry, Johannes Gutenberg-University, 55099, Mainz, Germany.
³ Fac Chem & Pharm, Sofia Univ. St Kliment Ohridski, 1 James Bourchier Blvd, Sofia, 1164, Bulgaria.
⁴ School of Materials Science and Engineering, Dongguan University of Technology, No. 1 Daxue Rd., Songshan Lake, Dongguan City, 523820 Guangdong Province, P. R. China.
⁵ Department of Microbiology, University of Ulsan College of Medicine ASAN Medical Center, Seoul 05505, South Korea.
⁶ Department of Chemistry, Pukyong National University, Busan, 48513, South Korea.

PMID: 37947588
DOI: 10.1002/anie.202315156

Abstract

A new class of near-infrared (NIR) fluorophores, PAI, is obtained by consecutive C-N/C-C bond formation between diphenylamines and 9,10-dibromoperylenecarboximide. Owing to the rigid structure, extended π-conjugation and pronounced push-pull substitution, these fluorophores show emission maxima up to 804 nm and large Stokes shifts. The extraordinarily high fluorescence quantum yields from 47 % to 70 % are attributed to chloro substitution in the bay positions of the perylene core. These characteristics, together with high photostability, qualify them as useful NIR emitters for applications as biomarkers and security inks.

Keywords: Biomarkers; Consecutive C−N/C−C Coupling Reactions; Fluorescence Quantum Yields; Near-Infrared; Rylenecarboximide.