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

被引：0

作者：

Wu, Ze-Hua ^{[1
,6
]}

Skabeev, Artem ^{[1
]}

Zagranyarski, Yulian ^{[3
]}

Duan, Ruomeng ^{[2
]}

Jin, Jun-O ^{[4
]}

Kwak, Minseok ^{[5
]}

Basche, Thomas ^{[6
]}

Muellen, Klaus ^{[1
,6
]}

Li, Chen ^{[1
,2
]}

机构：

[1] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany

[2] Dongguan Univ Technol, Sch Mat Sci & Engn, 1 Daxue Rd,Songshan Lake, Dongguan 523820, Guangdong, Peoples R China

[3] Univ Sofia, Fac Chem & Pharm, St Kliment Ohridski 1 James Bourchier Blvd, Sofia 1164, Bulgaria

[4] Univ Ulsan, Coll Med, ASAN Med Ctr, Dept Microbiol, Seoul 05505, South Korea

[5] Pukyong Natl Univ, Dept Chem, Busan 48513, South Korea

[6] Johannes Gutenberg Univ Mainz, Dept Chem, D-55099 Mainz, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 52期

关键词：

Biomarkers; Consecutive C-N/C-C Coupling Reactions; Fluorescence Quantum Yields; Near-Infrared; Rylenecarboximide; CHARGE SEPARATION; ACCEPTOR; DERIVATIVES; EMISSION; POLYMER;

D O I：

10.1002/anie.202315156

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 pi-conjugation and pronounced push-pull substitution, these fluorophores show emission maxima up to 804nm 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.

引用

页数：5

共 50 条

[41] Synthesis of 3-Substituted Quinazolinones via C-N and C-C bond Cleavage of Enaminone
Ambethkar, Sethurajan
Kalaiselvi, Mariappan
Padmini, Vediappen
Bhuvanesh, Nattamai
CHEMISTRYSELECT, 2017, 2 (19): : 5329 - 5332
[42] Selective Conversion of Unactivated C-N Amide Bond to C-C bond via Steric and Electronic Resonance Destabilization
Adebomi, Victor
Wang, Yuwen
Sriram, Mahesh
Raj, Monika
ORGANIC LETTERS, 2022, 24 (36) : 6525 - 6530
[43] Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
Lazaro-Milla, Carlos
Yanai, Hikaru
Almendros, Pedro
ORGANIC LETTERS, 2021, 23 (08) : 2921 - 2926
[44] Intermolecular C-H Aminocyanation of Indoles via Copper-iodine Cocatalyzed Tandem C-N/C-C Bond Formation
Yu, Wenhua
Zhang, Xiaoxiang
Liu, Chenrui
Zhang, Yingying
Gu, Xiaoting
Liao, Jiahao
Zhang, Zhuan
Wei, Wanxing
Li, Guanghua
Liang, Taoyuan
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18): : 12424 - 12433
[45] Intermolecular C-C/C-N σ-bond metathesis enabled by visible light
Li, Rujuan
Zhan, Renqin
Lang, Yatao
Li, Chao-Jun
Zeng, Huiying
CHEMICAL SCIENCE, 2024, 15 (32) : 12900 - 12905
[46] Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
Lanzi, Matteo
Merad, Jeremy
Boyarskaya, Dina V.
Maestri, Giovanni
Allain, Clemence
Masson, Geraldine
ORGANIC LETTERS, 2018, 20 (17) : 5247 - 5250
[47] REVERSIBLE INTERCONVERSION OF C-C AND C-N MULTIPLE BOND SYSTEMS ON CLUSTERS
BERNHARDT, W
VONSCHNERING, C
VAHRENKAMP, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03): : 279 - 280
[48] Cascade Formation of C3-Unsymmetric Spirooxindoles via PhI(OAc)2-Mediated Oxidative C-C/C-N Bond Formation
Sun, Jiyun
Li, Guangchen
Zhang, Guangtao
Cong, Ying
An, Xuechan
Zhang-Negrerie, Daisy
Du, Yunfei
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2476 - 2481
[49] Synthesis of highly functionalized organobismuth reagents and use in C-C, C-O, and C-N bond formation
Gagnon, Alexandre
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[50] C-C bond formation at ozonide rings by substitution of chlorinated ozonides
Griesbaum, K
Quinkert, RO
McCullough, KJ
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (17) : 3657 - 3662

← 1 2 3 4 5 →