Synthesis of C₃ Benzo[1,2‐e:3,4‐e′:5,6‐e′′]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium‐Catalyzed Arylation

Abstract

The C60 polyarenes 4, 5, 18 a, and 18 b have been synthesized from truxene by triple alkylation at C5, C10, and C15 followed by a palladium-catalyzed intramolecular arylation. The synthesis of "crushed fullerene" C60H30 (2) is the most efficient reported to date and proceeds in 33% overall yield.

A Pre‐organised Truxene Platform for Phosphorescent [Ru(bpy)2] and [Os(bpy)2] Metal Centres: A Clear‐Cut Switch from Förster‐ to Dexter‐Type Energy‐Transfer Mechanism

“…Unlike fluorene, which can only be used for building one‐dimensional chromophores, truxene can readily be functionalised in three directions in space to serve as an excellent building block for larger and dendritic structures. During the past decades truxene has been used as a potential starting material for the construction of liquid‐crystalline compounds,5, 6 bowl‐shaped fragments of fullerenes7 and C 3 ‐tripodal materials for chiral recognition 8. Recently synthesised truxene derivatives include a variety of star‐shaped oligomers and dendritic structures with extended π conjugation9 of the polyaromatic core, as well as truxene‐based donor–acceptor systems for use as multifunctional fluorescent probes 10.…”

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride

“…Derivatives 1a and 1b were readily prepared by the triple alkylation of the lithium anion of 4,9,14-trimethoxytruxene (Scheme 4) [41,62]. The cyclization reaction was carried out efficiently with gold(I) catalyst 6 (15 mol %) at room temperature in CH 2 Cl 2 to give triaryl substituted diacenaphtho[1,2- j :1',2'-l]fluoranthenes (decacyclenes) 2a and 2b in very good overall yields after aromatization of the crude products with DDQ.…”

Synthetic Routes to Electroactive Organic Discotic Aromatic Triazatruxenes

“…It is amazing that while its all‐carbon partner truxene has been broadly researched for the development of broadened hydrocarbons , electro‐optical devices , or liquid crystals , there was almost no study of the triindole . In 2006, Gόmez‐Lor et al .…”