Selective synthesis and (chir)optical properties of binaphthyl-based chiral carbon macrocycles
Pengwei Fang1, Muqing Chen2, Xinyu Zhang1
1Hefei National Research Center for Physical Sciences at the Microscale, Anhui Laboratory of Advanced Photon Science and Technology, CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, iChEM, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui Province, 230026, China. dupingwu@ustc.edu.cn.
Abstract:
Herein, we report the selective synthesis, characterization, and photophysical properties of two novel chiral carbon macrocycles. Non-planar (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene was introduced into the scaffold of oligo-paraphenylenes to achieve the chirality in these macrocycles. Their photophysical properties were investigated by steady-state and time-resolved spectroscopies, as well as circular dichroism and circularly polarized luminescence spectroscopies. We demonstrate that the emission maxima of the chiral macrocycles are redshifted compared to chiral binaphthyl units and that macrocycles show chiroptical properties (|glum| > 1.0 × 10-3).
Related Concept Videos
Prochirality
Chirality in Nature
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Stereoisomerism of Cyclic Compounds
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Woodward–Hoffmann Selection Rules and Microscopic Reversibility


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)