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.
Highlights
The synthesis of the first zig-zag O-doped molecular rhombic ribbon has been achieved
Building on this structural motif, one can conjecture that this approach could lead to polycyclic aromatic hydrocarbons (PAHs) featuring extended zig-zag peripheries
Indulging this line of thought, we put forward the first synthesis of a O-doped congener of 2,7-periacenoacene, in which six carbon atoms at the zig-zag edges have been replaced by oxygen atoms
Summary
The synthesis of the first zig-zag O-doped molecular rhombic ribbon has been achieved. The substitution of the carbon edges with heteroatoms[9] has provided a viable approach to prepare stable extended PAHs featuring zig-zag peripheries, and noticeable examples included O,[10] N-,[11]; OBO-,[12] NBN-[13] and BNB-doped[14] structures.
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