Cyclization of Pyrene Oligomers: Cyclohexa‐1,3‐pyrenylene

Abstract

First synthesis of the macrocycle cyclohexa(1,3-pyrenylene) is achieved in six steps starting with pyrene, leading to a non-aggregating highly twisted blue-light-emitting material. The cyclodehydrogenation of the macrocycle offers a promising synthesis route to holey-nanographene.

A macrocyclic oligofuran: synthesis, solid state structure and electronic properties

“…Introduction p-Conjugated macrocycles with well-dened diameters have received signicant attention in the last few decades, mainly because of their unique optical and electronic properties, their host-guest capabilities, and their potential as building blocks for supramolecular materials. [1][2][3][4][5][6] Many p-conjugated macrocyclic systems aggregate into columnar structures, 4,7-11 producing molecular channels that, with the appropriate inner-core functionalization, may give rise to ion channels, rod-like micellar aggregates, and even reaction chambers. [12][13][14][15] A particularly intriguing class of p-conjugated macrocycles is macrocyclic oligothiophenes (C-nT, Chart 1), introduced by Bäuerle's group in sizes ranging from C-8T to C-35T.…”

Macrocyclic 2,7‐Anthrylene Oligomers

“…[9] The next large acene unit suitable for hexagonal design is 2,7-anthrylene, and such frameworks as [6]cyclo-2,7-anthrylene ( [6]CANT, r = 1.97 nm) have been unknown to the best of our knowledge. [10][11][12] The studies of [6]CNAPi ndicated that in order to synthesize such al arge macrocycle, its structure should be modified so that reasonable solubility is maintained. In the courseo fo ur studies of anthracene-acetylene oligomers, [13] we found that bulky mesityl (Mes) groups on an anthracene unit reasonably improved the solubility and stability because those groups protected the aromatic cores from intermolecular stacking and undesired reactions.…”

1,3-Di(hetero)aryl-7-substituted Pyrenes—An Undiscovered Area of Important Pyrene Derivatives

“…Most of the described in literature pyrenes are 1,3,6,8-tetrasubstituted followed by 4,5,9,10-tetrasubstituted, 2,7-, and 1,6-, and 1,8-disubstituted pyrene derivatives [2][3][4][5]. In the case of 1,3-di(hetero)aryl-7-substituted ( Figure 1), there are only a few examples of derivatives containing at position 7-tert-butyl group [6][7][8][9]. These compounds exhibit interesting optical properties what caused that they were studied for use in the area of organic electronics.…”