Synthesis of Substituted Iptycenes

Abstract

Iptycenes are a class of aromatic compounds that contain several arene units fused to a bicyclo[2.2.2]octatriene bridgehead system. This unique, rigid, three-dimensional molecular structure provides several open electron-rich cavities with an abundance of reactive positions, and makes them useful for a wide range of applications. There is no doubt that the synthesis and reactions of iptycene derivatives with different functional groups form the fundamental basis of iptycene development. In this account, the synthesis of substituted iptycenes is described. In particular, the different synthetic strategies toward substituted triptycenes and pentiptycenes are the main focus. 1 Introduction 2 Synthesis of Substituted Triptycenes 2.

Recent advances in structurally elaborate triptycenes, triptycene-containing polymers and assemblies: structures, functions and applications

“…A reduction of 64 yields the 1,4-dihydroxypentiptycene monomer (63) [52], whereas a nucleophilic attack of 64 with a TMS-acetylide (65) and subsequent oxidation (66) and deprotection yields the 1,4diethynylpentiptycene monomer (58) [16,48]. However, it has been noted that the equivalent 1,4-diaminopentiptycene cannot be synthesized by a similar route [4,48,53].…”

“…Triptycene is a rigid molecule with a three-dimensional (3D) skeleton consisting of three phenylene rings arranged with interblade angles of 120°(Fig. 1a) [1][2][3][4][5][6][7][8][9][10]. Triptycene derivatives have been utilized in many fields, including supramolecular chemistry and polymer and materials science, and researchers have taken advantage of the structural features of triptycenes in the development of functional molecules, polymers, and assemblies.…”

1,5-Dichloroethanoanthracene Derivatives As Antidepressant Maprotiline Analogs: Synthesis, DFT Computational Calculations, and Molecular Docking

“…Based on 1,5-dichloroanthracene, many macrocyclic compounds have been synthesized and reported in the literature [7][8][9]. 1,5-dichloroanthracene was allowed to react with 3chlorobenzene through the Diels-Alder (DA) reaction to access substituted triptycene derivatives [10,11]. Starting from 1,5-dichloroanthracene and other anthracenes, a series of SiMe3-functionalized anthracene derivatives were synthesized via multistep cross-coupling reactions and NMRqualitatively studied towards UV irradiation [12].…”

Towards triptycene functionalization and triptycene-linked porphyrin arrays

“…Triptycene (1) consists of three benzene rings fused to a bicyclo[2.2.2]octane (BCO) skeleton, it is rigid, isolating and amenable to a wide range of chemical transformations. Due to the 120° rigid void, mono-, di-, tri-, tetra-, penta-and hexafunctionalizations of triptycene scaffolds can be achieved in a spatially defined manner ( Figure 1) [21][22][23]. Thus, a variety of functional groups can be presented in fixed orientations [24].…”