Stringing the Perylene Diimide Bow

Liu, Taifeng; Yang, Jingjing; Geyer, Florian; Conrad‐Burton, Felisa S.; Hernández Sánchez, Raúl; Li, Hexing; Zhu, Xiaoyang; Nuckolls, Colin P.; Steigerwald, Michael L.; Xiao, Shengxiong

doi:10.1002/ange.202004989

Stringing the Perylene Diimide Bow

Journal Article · Mon Jul 06 00:00:00 EDT 2020 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.202004989· OSTI ID:1637413

Liu, Taifeng ^[1]; Yang, Jingjing ^[2]; Geyer, Florian ^[2]; Conrad‐Burton, Felisa S. ^[2]; Hernández Sánchez, Raúl ^[2]; Li, Hexing ^[1]; Zhu, Xiaoyang ^[2]; ^[2]; Steigerwald, Michael L. ^[2]; Xiao, Shengxiong ^[1]

The Education Ministry Key Lab of Resource Chemistry Shanghai Key Laboratory of Rare Earth Functional Materials College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Department of Chemistry Columbia University New York NY 10027 USA

Abstract

This study explores a new mode of contortion in perylene diimides where the molecule is bent, like a bow, along its long axis. These bowed PDIs were synthesized through a facile fourfold Suzuki macrocyclization with aromatic linkers and a tetraborylated perylene diimide that introduces strain and results in a bowed structure. By altering the strings of the bow, the degree of bending can be controlled from flat to highly bent. Through spectroscopy and quantum chemical calculations, it is demonstrated that the energy of the lowest unoccupied orbital can be controlled by the degree of bending in the structures and that the energy of the highest occupied orbital can be controlled to a large extent by the constitution of the aromatic linkers. The important finding is that the bowing results not only in red‐shifted absorptions but also more facile reductions.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0014563

OSTI ID:: 1637413

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 34 Vol. 132; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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