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A π‐Extended Pentadecabenzo[9]Helicene

Yun‐Jia Shen, Nai‐Te Yao, Li‐Na Diao, Yang Yang, Xu‐Lang Chen, Han‐Yuan Gong

2023Angewandte Chemie International Edition104 citationsDOI

Abstract

Abstract A novel chiral nanographene (i.e. EP9H ) with a pentadecabenzo[9]helicene core fragment has been synthesized and fully characterized. Single‐crystal X‐ray diffraction unambiguously confirms the helical structure. The fluorescence emission of EP9H is located in the near infrared region ( λ em =684 nm) with a medium quantum yield (0.10) for helicene derivatives. Cyclic voltammetry reveals its seven quasi‐reversible redox states from −2 to +5. Furthermore, enantiopure EP9H displays distinct CD signals in a broad spectral range from 300 to 700 nm. Notably, compared to the reported small organic molecules, EP9H displays an outstanding | g lum | value of 4.50×10 −2 and B CPL as 304 M −1 cm −1 .

Topics & Concepts

HeliceneEnantiopure drugCyclic voltammetryCrystallographyQuantum yieldMoleculeFluorescenceYield (engineering)ChemistrySingle crystalRedoxMaterials scienceStereochemistryElectrochemistryPhysicsOrganic chemistryEnantioselective synthesisPhysical chemistryOpticsElectrodeMetallurgyCatalysisSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryPorphyrin and Phthalocyanine Chemistry