Oxygen‐Doped Zig‐Zag Molecular Ribbons. Issue 29 (19th June 2018)

• Record Type: Journal Article
• Authors: Berezin, Andrey; Biot, Nicolas; Battisti, Tommaso; Bonifazi, Davide
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 29(2018)
• Page Start: 8942
• Page End: 8946
• Publication Date: 2018-06-19
• Subjects: C−O bond formation -- Cu-catalyzed cycloeterification -- heteroatom doping -- nanoribbons -- supramolecular chemistry -- Zig-zag peripheries; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201803282
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The synthesis of a zig‐zag oxygen‐doped molecular rhombic ribbon has been achieved. This includes oxidative C−C and C−O bond formations that allowed the stepwise elongation and planarization of an oxa‐congener of 2, 7‐periacenoacene. X‐ray diffraction analysis corroborated the flat structure and the zig‐zag topology of the O‐doped edges. Photophysical and electrochemical investigations showed that the extension of the peri‐xanthenoxanthene (PXX) into the molecular ribbon induces a noticeable shrinking of the molecular band gap devised by a rising of the HOMO energy level, a desirable property for p‐type organic semiconductors. Abstract : A zig‐zag oxygen‐doped molecular rhombic ribbon was synthesized, involving oxidative C−C and C−O bond formations that allowed elongation and planarization of a oxa‐congener of 2, 7‐periacenoacene. The extension of peri‐xanthenoxanthene (PXX) into the molecular ribbon was shown to induce a noticeable shrinking of the molecular band gap, a desirable property for p‐type organic semiconductors.