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

• Published in: Angewandte Chemie International Edition Vol. 62; no. 52; pp. e202315156 - n/a
• Main Authors: Wu, Ze‐Hua, Skabeev, Artem, Zagranyarski, Yulian, Duan, Ruomeng, Jin, Jun‐O, Kwak, Minseok, Basché, Thomas, Müllen, Klaus, Li, Chen
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.12.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Biomarkers; Bonding; Chemical compounds; Chemistry; Chemistry, Multidisciplinary; Conjugation; Consecutive C−N/C−C Coupling Reactions; Emitters; Fluorescence; Fluorescence Quantum Yields; Fluorophores; Inks; Near infrared radiation; Near-Infrared; New class; Physical Sciences; Rigid structures; Rylenecarboximide; Science & Technology; Substitutes; Consecutive C-N/C-C Coupling Reactions; POLYMER; Biomarkers; CHARGE SEPARATION; Rylenecarboximide; EMISSION; Fluorescence Quantum Yields; Near-Infrared; DERIVATIVES; ACCEPTOR; Consecutive C−N/C−C Coupling Reactions
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202315156

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. A new class of near‐infrared (NIR) fluorophores is obtained by consecutive C−N/C−C bond formation between diphenylamines and 9,10‐dibromoperylenecarboximide. These fluorophores show high fluorescence quantum yields, together with large Stokes shifts and high photostability, qualifying them as useful NIR emitters for applications as biomarkers and security inks.