Regioconvergent Synthesis of a π-Extended Tribenzotriquinacene-Based Wizard Hat-Shaped Nanographene

Abstract

The successful enlargement of the curved π-electron periphery of the wizard hat-shaped polycyclic aromatic compound 1 is described. The target structure 2 features an m,m,p,m,m,p,m,m,p-nonaphenylene belt fused to a central tribenzotriquinacene unit. The synthesis involves a multiple regioconvergent Scholl-type dehydrocyclization as the key step. Spectroscopic, structural, and electronic properties of the title compound 2 are reported.

Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review

“…This DDQ-induced methodology has paved the way to design and synthesize electron-rich p-conjugated aromatics with the combination of ve-, six-, and seven-membered carbocycles with interesting optical and electronic properties. 88 From the abovementioned discussion, it is concluded that DDQ has excellent oxidant oxidizing capacity as compared to FeCl 3 and AlCl 3 . Its reduction potential value is +0.50 V.…”

“…This DDQ-induced methodology has paved the way to design and synthesize electron-rich π-conjugated aromatics with the combination of five-, six-, and seven-membered carbocycles with interesting optical and electronic properties. 88 …”

The Scholl Reaction as a Powerful Tool for Synthesis of Curved Polycyclic Aromatics

“…Further oxidation of 191 with DDQ (3.0 equiv)/CF 3 SO 3 H afforded 190 in a yield of 61% yield. Bromination of 190 and the subsequent Suzuki coupling with phenylboronic acid gave the hexaphenyl derivative of 190 as a mixture of regioisomers, which was oxidized by DDQ/CF 3 SO 3 H to afford the 3-fold π-extended product 192 in a yield of 38% with formation of 9 C–C bonds . Because the precursor to 192 is a mixture of regioisomers, the red bold lines in the structure of 192 (Figure ) only represent the bond formation from a particular regioisomer.…”

DDQ as a versatile and easily recyclable oxidant: a systematic review

“…This DDQ-induced methodology has paved the way to design and synthesize p-electrons rich conjugated aromatics with a combination of ve-, six-, and eight-membered carbocycles having improved optical and electronic properties. 106 The main challenge in the condensation of polyphenylenes into planar-and non-planar nanographenes lies in the complete removal of hydrogens in order to make multiple C-C bonds. In this context, several oxidant systems including iron chloride, vanadium chloride, and copper chloride have been used to achieve this goal.…”

“…This DDQ-induced methodology has paved the way to design and synthesize π-electrons rich conjugated aromatics with a combination of five-, six-, and eight-membered carbocycles having improved optical and electronic properties. 106 …”