Synthetic Strategies for Dehydrobenzo[n]annulenes

Abstract

Dehydrobenzoannulenes have accrued great interest due to their potential uses such as hosts for binding guest molecules and precursors to fullerenes and other carbon‐rich materials, as well as their unique properties such as conductivity or superconductivity and nonlinear optical effects. These systems have seen numerous synthetic strategies employed in their construction over the past 50 years. As alkyne chemistry has developed more recently, annulene networks with greater complexity have been possible and the field has seen a vast resurgence. This article gives an account of synthetic methods developed for the preparation of annulenic systems and describes some of the interesting observed properties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

All‐Carbon Scaffolds by Rational Design

“…[30] While both 2 and 3 have not yet been prepared, reasonable synthetic approaches to smaller and larger substructures of these carbon networks have been proposed and developed. [31] Graphdiyne could conceivably be synthesized by controlled cyclotrimerization of cyclo-C 18 on surfaces, as previously proposed. [23] Today, molecular-resolution imaging by scanning tunneling microscopy (STM) enables the monitoring of the assembly of macrocyclic p-systems on surfaces.…”

An Extremely Simple Dibenzopentalene Synthesis from 2‐Bromo‐1‐ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities

“…[5] The dibenzopentalene synthesis starting from 2-halo-1-ethynylbenzenes is quite attractive from the viewpoint of synthetic chemistry because of the high availability of the starting materials and the formation of three CÀC bonds in one process. It has been known that nickel(0) complexes effectively catalyze the Ullman-type coupling of aryl halides.…”

Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups

“…Regarding their highly conjugated structure, these compounds have intensively been studied [8][9][10][11][12][13][14] as promising candidates for innovative electronic and photonic materials [15]. The donor/ acceptor dehydrobenzo [18]annulenes attracted special interest given that this kind of push-pull systems is good candidates for use in non-linear optics [16,17].…”