Synthesis and Properties of Ethylene-Annulated Di(perylene diimides)

Abstract

A new synthetic method toward ethylene-annulated di(perylene diimides) from easily available ethylene-annulated di(perylene esters), which is conducted by ICl-induced cyclization and Mizoroki-Heck coupling of ethynylene-linked di(perylene esters), is reported.

Progress in the synthesis of perylene bisimide dyes

“…The latter compounds represent the key building blocks in the synthesis of fused dimeric PBIs and PBI nanoribbons, 149 in addition to ethylenefused polymers, 150,151 although it should be pointed that the synthetic route for the preparation of the first ethynylene-fused dimeric PBI involved cyclization of alkyne-bridged PTE. 152 Ethenyl-bridged dimeric PBI 134 was synthesized in 88% yield by coupling of bromo-PBI 7g with 0.5 equivalent of 1,2-bis(tributylstannyl)ethylene, using Pd(PPh 3 ) 4 as a catalyst (Scheme 39). 149 These methods can be extended to the synthesis of higher oligomers.…”

Consecutive Supramolecular Polymerization of a Rylene‐Based Twistacene

“…To investigate the supramolecular polymerization of twistacene 1 , we have initially utilized UV/Vis spectroscopy by using a variety of solvents and at a total concentration ( c T ) of 10 μ m . In “good” solvents like CHCl 3 and 1,1,2,2‐tetrachloroethane (TCE), the UV/Vis spectra of 1 show the typical pattern for vibronic transitions of perylene bisimides (PBIs) and closely related twistacenes with absorption maxima at λ =551, 515, 474 and 387 nm, diagnostic of molecularly dissolved species (Figure a and Supporting Information, Figure S1). The fluorescence spectrum of monomeric 1 , registered in CHCl 3 as solvent, displays a maximum at λ =559 and 601 nm resembling a mirror image of the absorption spectrum (Figure b and the Supporting Information, Figure S2).…”

Color Bricks: Building Highly Organized and Strongly Absorbing Multicomponent Arrays of Terpyridyl Perylenes on Metal Oxide Surfaces

“…The synthetic route to 1,7‐substituted PMI 14 is shown in Scheme . Perylene tetraester (PTE) 8 was obtained in 84 % yield by esterification of commercially available perylenetetracarboxylic dianhydride ( 7 ) with a homogeneous solution of butanol and 1‐bromobutane by following a literature procedure . PTE 8 was brominated in the presence of a base and molecular bromine in CH 2 Cl 2 at room temperature.…”

“…Perylene tetraester (PTE) 8 was obtainedi n8 4% yield by esterification of commerciallya vailable perylenetetracarboxylic dianhydride (7)w ith ah omogeneous solution of butanol and 1-bromobutane by followingaliterature procedure. [19] PTE 8 wasb rominatedi nt he presence of ab ase and molecular bromine in CH 2 Cl 2 at room temperature. Dibromo PTE 9 was obtainedi n9 1% yield as am ixture of 1,7-and 1,6regioisomers (4:1).…”