Synthesis and Chiroptical Properties of Chiral Helical Foldamers Based on Highly Fluorescent Dibenzopyrrolo[1,2‐<i>a</i>][1,8]naphthyridines Linked to a Tetraphenylene Core
Abstract Fluorescent L‐shaped dibenzopyrrolo[1,2‐ a ][1,8]naphthyridine units were linked to a tetraphenylene core to create chiral bishelical foldamers. X‐ray crystallography revealed that the foldamer 2TP syn , with two L‐shaped units, adopted a helical structure with a single‐handed helicity due to the axial chirality based on a 2,15‐substituted tetraphenylene core. Notably, the chiral foldamers 4TP , 2TP syn, and 2TP anti exhibited fluorescence with high quantum yields ( ϕ > 0.8) and circularly polarized luminescence, demonstrating that the axial chirality of chiral tetraphenylenes based on the substitution pattern induced chiroptical properties to the fluorescent units.
Authors
- Masashi Hasegawa (ORCID: https://orcid.org/0000-0003-3302-6496)
- Hidetoshi Kawai (ORCID: https://orcid.org/0000-0002-3367-0153)
- Yoshitaka Tsuchido (ORCID: https://orcid.org/0000-0001-8860-0745)
- Kotaro Matsumura
Institutions
- Tokyo University of Science (JP)
- Kitasato University (JP)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-04-24
- DOI
- https://doi.org/10.1002/ajoc.202500409
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.81
Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science