Ladder-like polyacetylene with excellent optoelectronic properties and regular architecture

Abstract

Novel double-stranded polyacetylene with a perylene bisimide bridge has been efficiently synthesized by metathesis cyclopolymerization of bis(1,6-heptadiyne) derivatives, and exhibited good solubility, highly thermal and oxidative stability, low LUMO energy levels, narrow bandgaps, and regular ladder-like architecture.

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

“…[2.2.1]Bicyclohept-5-enederivatives (norbornenes) are the most common monomers in ROMP, as a huge variety of different monomers can be [15][16][17], pentacene [18], tetracene [18] Anthracene [15,17], pyrene [19], benzothienobenzothiophene [20] --Anthracene [74] Fluorene [90] (Hetero)cycles Perylene bisimides [21][22][23][24], hexabenzocoronene [25][26][27], quinolone [26], pyrene [29] Phenanthroimidazole [30,31] perylene bisimides [21], quinizarine [32], phenoxynaphthacene [33] Perylene bisimides [21] Phenanthroimidazole [11], perylene bisimides [8], pyrene [9] Coumarin [79] Benzoxazole [81] Benzoxazole [76,90] a Triphenylmethane dyes (Dichloro)fluorescein [40], eosin [40] Eosin [41] Oregon Green 488 [42], rhodamin B [43], rhodamin [44], fluorescein [44], eosin [45][46][47] Fluorescein [10] Rhodamin, [10,…”

“…A wide range of suitable monomers has been copolymerized comprising (hetero)polyaromatic compounds [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33], and more sophisticated functionalities like conjugated oligomers [34][35][36][37][38][39], triphenylmethane [40][41][42][43][44][45][46][47], azo [48][49][50][51][52], or polymethine [53][54][55][56][57] dyes. Even transition metal coordination compounds of aluminum [58,59], iron [60], zinc [61][62][63], ruthenium [64, 65], europium …”

“…11). Unlike for the hexabenzocoronenes, the perylene moieties were aligned in different directions and the resulting ladder polymers ended up to be amorphous as shown by TEM analysis [24]. The aggregation of perylenes is varying depending on the chemical environment and this in turn influences the optical properties of a material in different solvents and in film [22].…”

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…75) [360,361], nucleic acid bases attached to an aminoethylglycine support [362], alkoxyquinoline groups (e.g. 77) [363], fluorescent groups and PEG groups (copolymer) [364]; polyoxometallates [365], dendriditically connected to a polylactate and a polystyrene system [366], and dendritic connection to anthraquinone moieties [367]; (19) bis(norbornenesuccinimide)s connected through a perylene ring [368]; (20) aza-Diels-Alder derived azanorbornenes (e.g. 80) [369]; (21) oxanorbornenes connected to azide groups [370]; (22) oxanorbornenecuccinic anhydride (81) [371]; (23) oxanorbornenesuccinimides, including those connected to alkyne groups [372], and to dendrimeric systems [373,374]; and (24) oxanorbornenedicarboxylate esters connected to guanidine groups [375].…”

Azobenzene‐Incorporated Single‐ and Double‐Stranded Polynorbornenes: Facile Synthesis and Diverse Photoresponsive Property

“…Structurally, it can be considered as a multiple stranded polymer with a linear array of cofacially oriented linkers. The ladder‐type arrays in ladderphanes should be orthogonal to the polymeric strands and have planar and rigid π–π structures that facilitate electron delocalization and enhance conjugation . Unlike most ladder polymers where each repeat unit is connected by two bonds, the linkers in covalently bonded ladderphanes are orthogonal to the polymeric strands and can be planar aromatic, macrocyclic metal complexes, or 3D organic or organometallic moieties.…”