Uniform Half-Substituted Chiral Arylcycloparaphenylene: Synthesis, Crystal Structure, and Chiroptical Properties
Wen Zhang1, Jinyi Wang1, Xinyu Zhang1
1Key Laboratory of Precision and Intelligent Chemistry, Hefei National Research Center for Physical Sciences at the Microscale, Department of Materials Science and Engineering, School of Applied Chemistry and Engineering, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui Province, 230026, P.R. China.
None:
The strategic implementation of aryl-functionalization in every phenyl group in organic architectures presents a transformative approach to constructing novel molecular nanocarbon materials. In this present work, we demonstrate the first synthesis of a uniform and chiral half-aryl substituted cycloparaphenylene (CPP), [6]CPP-12tBuPh. Single-crystal X-ray diffraction analysis unambiguously confirms its hoop-shaped structure and the existence of planar chirality arising from stereochemically distinct substituent orientations. The resolved pS and pR enantiomers display mirror-imaged circular dichroism (CD) signals and a high luminescence dissymmetry factor (|glum| = 2.6 × 10⁻2). Photophysical characterization reveals the emergence of aggregation-induced emission (AIE) behavior, with pure [6]CPP-12tBuPh powder sample exhibiting intense orange fluorescence.
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