Oligothiophene‐Ring‐Strapped Perylene Bisimides: Functionalizable Coaxial Donor–Acceptor Macrocycles. (12th December 2022)

• Record Type: Journal Article
• Authors: Dnyaneshwar Veer, Sairam; Chandrakant Wakchaure, Vivek; Asokan, Kiran; Dixit, Ruchi; Goswami, Tanmay; Saha, Ramchandra; Gonnade, Rajesh; Ghosh, Hirendra N.; Santhosh Babu, Sukumaran
• Is Part Of: Angewandte Chemie. Volume 135:Number 3(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-12
• Subjects: Charge Separation -- Donor–Acceptor Systems -- Electron Transfer -- Macrocycles -- Perylene Bisimides; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202212934
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Aesthetic designs from nature enable new knowledge to be gained and, at the same time, inspire scientific models. In this context, multicomponent macrocycles embody the advantage of precisely positioning the structural units to achieve efficient communication between them. However, the construction of a functionalizable macrocycle for ultrafast charge separation and stabilization has not been attempted. Herein, we report the synthesis, crystal structure, and transient absorption of a new functionalizable macrocycle consisting of an oligothiophene‐ring‐strapped perylene bisimide. Transient absorption results point to a sequential improvement in charge separation and stabilization from the macrocycle to the corresponding linear dimer and 2D polymer due to the unique design. Our macrocycle design with a supportive spatial arrangement of the donor and acceptor units will inspire the development of more complex synthetic systems with exciting electron‐transfer and charge‐separation features. Abstract : A new macrocycle consisting of oligothiophene‐ring‐strapped perylene bisimide was synthesized, and the perpendicular donor–acceptor orientation was confirmed by single‐crystal analysis. This functionalizable macrocycle enabled the synthesis of the corresponding linear dimer and 2D polymer. The precise positioning and preferred orientation of donor and acceptor units in this macrocycle led to ultrafast electron transfer and long‐lived charge separation.