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Uniform Half‐Substituted Chiral Arylcycloparaphenylene: Synthesis, Crystal Structure, and Chiroptical Properties

Wen Zhang, Jinyi Wang, Xinyu Zhang, Bing Yuan, Pengwei Fang, Nan Yin, Pingwu Du

2025Angewandte Chemie International Edition11 citationsDOI

Abstract

Abstract 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‐12 t BuPh . 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 (| g lum | = 2.6 × 10⁻ 2 ). Photophysical characterization reveals the emergence of aggregation‐induced emission (AIE) behavior, with pure [6]CPP‐12 t BuPh powder sample exhibiting intense orange fluorescence.

Topics & Concepts

ArylPlanar chiralityChirality (physics)SubstituentCircular dichroismEnantiomerLuminescenceCrystal structureMaterials scienceCrystallographyFluorescenceStereochemistryChemistryEnantioselective synthesisOpticsOrganic chemistryOptoelectronicsChiral symmetryPhysicsQuantum mechanicsQuarkCatalysisAlkylNambu–Jona-Lasinio modelSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsPolydiacetylene-based materials and applications
Uniform Half‐Substituted Chiral Arylcycloparaphenylene: Synthesis, Crystal Structure, and Chiroptical Properties | Litcius