A helically twisted ribbon-shaped nanographene 3 containing four pentagons, eighteen hexagons and four heptagons was synthesized by a cascade of classical Scholl and non-classical Scholl-type cycloheptatriene formation reactions. In the...
Our recent research efforts on the synthesis of nonplanar nanographenes bearing tribenzotriquinacene or fenestrindane skeleton are summarized. Wizard hat-shaped or saddle-shaped nanographenes could be prepared using a non-classical Scholl-type cycloheptatriene formation or 19-membered ring macrocyclization. The key to the success of these transformation relies on the proper installation of the electron rich aryl functional groups in the bay areas of these molecular motifs. The three-dimensional structures of some of the nanographenes were determined by X-ray crystallography. Furthermore, these carbon-rich π-conjugated molecules are also showed to have interesting photophysical, self-assoication and host-guest complexation properties.
1,5,9‐Tribromo‐2,3,6,7,10,11‐hexamethoxy‐4b1‐methyltribenzotriquinacene, a C3‐symmetric TBTQ derivative, can be prepared conveniently and with high regioselectivity from readily available starting materials. It is a versatile key compound for the synthesis of other chiral 1,5,9‐trifunctionalized TBTQ derivatives and π‐extended congeners in which the bays of the TBTQ skeleton are bridged by vinylene and 1,2‐arylene units. X‐ray crystal structure analysis and UV‐vis spectroscopy show that vinylene bay‐bridging enables better π‐conjugation with the arene rings of the TBTQ core than 1,2‐arylene bay‐bridging does.
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