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Double π‐Extended Undecabenzo[7]helicene

Ying Chen, Chaojun Lin, Zhi-Xing Luo, Zhibo Yin, Haonan Shi, Yanpeng Zhu, Jiaobing Wang

2021Angewandte Chemie International Edition118 citationsDOI

Abstract

Abstract This work reports the first double π‐extended undecabenzo[7]helicene 1 , which is a large chiral nanographene, composed of 65 fused rings and 186 conjugated carbon atoms. The molecular identity of 1 has been confirmed by single crystal X‐ray diffraction. A wine coloured solution of 1 in dichloromethane absorbs light from ultraviolet to the near infrared, featuring an extremely large molar absorption coefficient of 844 000 M −1 cm −1 at 573 nm. Optically pure 1 shows a record high electronic circular dichroism intensity in the visible spectral range (|Δ ϵ |=1375 M −1 cm −1 at 430 nm) known for any discrete polycyclic aromatic hydrocarbon. These unusual photophysical properties of 1 contrast sharply with those of a mono‐undecabenzo[7]helicene derivative 2 .

Topics & Concepts

HeliceneFluorescenceCrystallographyAbsorption (acoustics)Conjugated systemMaterials scienceUltravioletCircular dichroismCrystal (programming language)ChemistryDichloromethanePhotochemistryMoleculeOpticsOrganic chemistryPolymerOptoelectronicsPhysicsComposite materialComputer scienceProgramming languageSolventSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryDNA and Nucleic Acid Chemistry