Synthesis of Optically Active Folded Cyclic Dimer and Trimer

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry Optically active higher-ordered structures, such as one-handed helical and propeller-shaped structures, can be constructed by folding the π-conjugated system using [2.2]paracyclophane as the chiral crossing unit, leading to circularly polarized luminescence (CPL) properties. Chiral cyclic dimers and trimers were synthesized using planar chiral [2.2]paracyclophane-containing enantiopure ribbon-shaped compounds as the chiral monomers. π-Conjugated systems were folded at the [2.2]paracyclophane units, and exhibited good photoluminescence quantum efficiencies and CPL anisotropy factors. Opposite chiroptical properties were observed between the dimer and trimer, despite the same absolute configuration of the planar chiral [2.2]paracyclophane units, which was reproduced by theoretical studies.

Planar chirality, [2.2]paracyclophane, circularly polarized luminescence, oligomer | Format: PDF | Size: 3.3 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Kumamoto, E.; Ogawa, K.; Okamoto, K.; Morisaki, Y. Beilstein Arch. 2025, 202538. doi:10.3762/bxiv.2025.38.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2025 Kumamoto et al.; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.