[3]CycloBODIPY: A Highly Strained Cyclic BODIPY Trimer with Effective Macrocyclic Conjugation
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<sup>-1</sup>, 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.
Authors
- Hideaki Takano (ORCID: https://orcid.org/0000-0003-0744-9292)
- Ichiro Hisaki (ORCID: https://orcid.org/0000-0002-8170-5605)
- Ryutaro Maeda (ORCID: https://orcid.org/0000-0003-1693-0790)
- Hiroshi Shinokubo (ORCID: https://orcid.org/0000-0002-5321-2205)
- M. Sugino
- Yoshitaka Tsuchido (ORCID: https://orcid.org/0000-0001-8860-0745)
Institutions
- Tokyo University of Science (JP)
- Toneyama National Hospital (JP)
- Japan Chemical Innovation and Inspection Institute (JP)
- Nagoya University (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-10-21
- DOI
- https://doi.org/10.1002/anie.202519612
- Citations
- 4
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 2.07
Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science