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Tuning the Twist by Molecular Design: A New Strategy for Hexabenzocoronene-Containing Helical Twistacene
Juan P Mora-Fuentes1,2, Daniel Villar-Castro1, J Francisco Barbosa-de-Bessa1
1Centro Singular de Investigación de Química Biológica y Materiales Moleculares (CiQUS) and Departamento de Química Orgánica, Universidad De Santiago de Compostela, Santiago de Compostela, Spain.
None:
In this work, we present an efficient synthetic methodology that allows precise and selective control on the C-C bonds during the Scholl reaction. The first ever described hexabenzocoronene (HBC)-containing helical twistacene NG2 has been obtained with very high yield and practically no need for purification, starting from a helical-twisted hexacene NG1. X-ray analysis reveals an end-to-end twist angle, from approximately 145° in NG1 to 132° in NG2. This approach has provided access to nanographenes (NGs) with improved properties compared to their planar analogues, in particular, enhanced solubility and high stability. In addition, they exhibit interesting redox properties, which, together with their high molar absorbance and optimal energy levels, highlight their potential as new organic semiconductor materials for emerging photovoltaic and electronic technologies.
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