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Triple Oxa[7]helicene with Circularly Polarized Luminescence: Enhancing the Dissymmetry Factors via Helicene Subunit Multiplication

Fulin Zhou, Zhenmei Huang, Zhongyan Huang, Rui Cheng, Yudong Yang, Jingsong You

2021Organic Letters49 citationsDOI

Abstract

The development of multiple heterohelicenes with a high luminescence dissymmetry factor (glum) is an appealing yet challenging task. Herein, we disclose the synthesis of a structurally unusual furan-based triple oxa[7]helicene, which represents the first reported triple hetero[7]helicene, via [2+2+2] cyclotrimerization/intramolecular dehydrogenative annulation. Compared to the reported double oxa[7]helicene, the triple oxa[7]helicene exhibits an improved glum value of 1.8 × 10–3, exemplifying the potential of the helicene subunit multiplication approach to enhance the glum of heterohelicenes.

Topics & Concepts

HeliceneChemistryIntramolecular forceLuminescenceStereochemistryMoleculeMaterials scienceOrganic chemistryOptoelectronicsSynthesis and Properties of Aromatic CompoundsAdvanced NMR Techniques and ApplicationsPhotochromic and Fluorescence Chemistry
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