Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and Highly Substituted Nanographenes from Simple Aromatics

Abstract

A facile and efficient self-sorting assemble (CSA) strategy has been paved for bottom-up construction of the 3-fold symmetrical and highly substituted hexa-cata-hexabenzocoronenes (c-HBCs), the trithieno analogues, and larger disc-shaped PAHs from simple chemicals using benzylic carbons as tenon joints and a novel FeCl3-mediated AAA process as a key step. The structures of the as-prepared c-HBCs and related NGs were clearly identified by spectral analyses and X-ray crystallographic studies. Moreover, these can be envisaged to serve as new launching platforms for the construction of larger and more complex π-conjugated molecules and supramolecular architectures because of the modifiable and symmetrical decorations.

An Electron‐Poor C64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

“…Instead, the overall mean bond length of 1 (1.413 Å) is comparable to that of infinite graphene (1.415 Å),23 although the benzenoid C−C bonds (1.409 Å; Figure 1 c, shaded in red) are somewhat shorter than the interconnecting carbon–carbon bonds (1.436 Å; Figure 1 c, marked in blue). Similar bond‐length characteristics have been observed for disc‐shaped nanographenes14 and coronenes24 by X‐ray analysis. With an almost coplanar π‐surface of approximately 118 Å 2 that is generated by 64 fully conjugated carbon and 4 nitrogen atoms, compound 1 is one of the largest planar PAHs whose molecular structure has been determined by X‐ray analysis.…”

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

“…Wei and co‐workers developed a convenient method for the synthesis of threefold symmetrical nanographenes 153 and 154 by reacting 1,3,5‐tribenzylbenzene derivatives 152 with aromatic aldehydes in the presence of FeCl 3 as a catalyst/oxidant and acetic anhydride as a dehydrant in a CH 2 Cl 2 /CH 3 NO 2 mixture (Scheme ) . The reaction is a combination of Friedel–Crafts‐type substitution (between formyl groups of aldehydes and aryl rings), dehydrogenative aromatization, and intramolecular oxidative coupling and produces the nanographenes 153 and 154 a – c in good yields.…”

New method for the synthesis of a highly-conjugated acene material and its application in Perovskite solar cells

“…17 Herein, we report the rapid transformation of oligonaphthalenes to nanographene-like structures, which have different conjugation lengths. Compared with the traditional synthetic methods, such as bromination and Suzuki coupling, used to synthesize acene, 18 this synthetic route is shorter since it has only two steps. This research could be applied in the synthesis of nanographene materials.…”