[3]CycloBODIPY: A Highly Strained Cyclic BODIPY Trimer with Effective Macrocyclic Conjugation
Abstract
Abstract Cyclic oligomers containing porphyrinic chromophores have attracted significant attention in broad areas of science as artificial models for photosynthetic light‐harvesting antennae due to their structural and functional resemblance to natural chlorophyll arrays. Here, the synthesis of a macrocyclic [3]cycloBODIPY derivative, which consists of only boron‐dipyrromethene (BODIPY) units, via an Au‐mediated macrocyclization protocol is reported. While this [3]cycloBODIPY derivative exhibits a high total strain energy of 86.4 kcal mol −1 , part of the intrinsic strain is effectively dispersed due to the flexible boron centers. Furthermore, this [3]cycloBODIPY derivative exhibits near‐infrared (NIR) absorption reaching 1050 nm as the result of two electronic modulation factors, i.e., deformation of the BODIPY subunits and effective π‐conjugation over the entire macrocycle.
Article Details
Authors (6)
Masaki Sugino
Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University Chikusa‐ku Nagoya 464‐8603 Japan
Yoshitaka Tsuchido
Department of Chemistry Faculty of Science Tokyo University of Science 1–3 Kagurazaka Shinjuku‐ku Tokyo 162–8601 Japan
Rento Maeda
Division of Chemistry Graduate School of Engineering Science The University of Osaka 1–3 Machikaneyama Toyonaka Osaka 560‐8531 Japan
Ichiro Hisaki
Graduate School of Engineering Science
Hideaki Takano
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Integrated Research Consortium on Chemical Sciences (IRCCS), and Research Institute for Quantum and Chemical Innovation, Institutes of Innovation for Future Society, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan
Hiroshi Shinokubo
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering