Switching the Photoluminescence and Electrochemiluminescence of Liposoluble Porphyrin in Aqueous Phase by Molecular Regulation

• Published in: Angewandte Chemie Vol. 132; no. 51; pp. 23461 - 23467
• Main Authors: Zhang, Yinpan, Zhao, Yaqi, Han, Zhengang, Zhang, Ruizhong, Du, Peiyao, Wu, Yanxia, Lu, Xiaoquan
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 14.12.2020
• Subjects: Agglomeration; aqueous phase; Aqueous solutions; Chemistry; Electrochemiluminescence; Luminescence; molecular regulation; Molecular structure; Photoluminescence; Photons; porphyrin; Porphyrins
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.202010216

By a facile peripheral decoration of 5‐(4‐aminophenyl)‐10,15,20‐triphenylporphyrin (ATPP) with inherent aggregation‐induced emission (AIE) active tetraphenylethene (TPE), a versatile AIEgenic porphyrin derivative (ATPP‐TPE) was obtained, which greatly abolishes the detrimental π–π stacking and thus surmounts the notorious aggregation‐caused quenching (ACQ) effect of ATPP in aqueous phase. The photoluminescence of ATPP‐TPE is 4.5‐fold stronger than ATPP at aggregation state. Moreover, an unequivocal aggregation induced electrochemiluminescence (AIECL) of ATPP‐TPE was found to be seriously dependent on its aggregation property in aqueous solution with efficiency of 34 %, which is 6 times higher than pure ATPP. The versatility of this molecular structure modulation strategy along with the ACQ‐to‐AIE transformation in this work provides direction to guide for applying liposoluble porphyrins in aqueous phase by designs of synthetic porphyrin AIEgens. A porphyrin derivative was designed to be used in electrochemiluminescence (ECL), and the highly efficient aggregated state ECL of the water‐insoluble porphyrin in aqueous environment was realized. The problem of traditional porphyrins as bio‐probe molecule aggregation‐caused quenching was solved.