Hexa-peri-hexabenzocoronene (HBC)-Incorporated Single- and Double-Stranded Polynorbornenes

Abstract

Double-stranded polymeric ladderphane 1 using HBC as linkers and the single-stranded comblike polynorbornene 2 with HBC pendants are synthesized by the ring-opening metathesis polymerization using the first-generation Grubbs catalyst. The photophysical properties of these HBC-incorporated polymers indicate significant interactions between adjacent polynuclear aromatic chromophores which are comparable with those of aggregated forms of the HBC cores. No liquid crystal properties, however, are observed in these polymers. The STM images of 1 and 2 demonstrate the unique properties of polynorbornene derivatives having N-aryl-5,6-endopyrrolidene pendants or linkers where the polymers are self-assembled to form ordered two-dimensional arrays on the HOPG surface.

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

“…11) have been synthesized and selfassembled patterns were studied by scanning tunneling microscopy (STM) [27]. While the monomers arranged into a similar pattern with face-on morphology as observed for unsubstituted HBC, the ladder polymers attained a rodlike structure.…”

“…[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 …”

Synthesis of ladder‐like polynorbornenes with n‐type perylenendiimide derivatives as bridges

“…Moreover, we employed ring‐opening metathesis polymerization (ROMP), which has been demonstrated an efficient method to prepare polymers with high molecular weight and complicated architectures in spite of the steric bulk of monomers 23–25. For example, Luh and coworkers reported the ROMPs of endo‐fused norbornene derivatives catalyzed by Grubbs‐I catalyst can give the corresponding polynorbornenes with ladder‐like backbones 26. Cheng and coworkers applied ROMP and ROP to prepared molecular bottlebrush with polynorbornene as backbone and polypeptide as side chain via one‐pot reaction 27.…”

Hexa-peri-hexabenzocoronene in organic electronics

“…2) [51]. Pendant and ladder-type polymers containing HBC units have been reported with a polynorbornene backbone 17 [52]. Electron acceptor perylene monoimide was covalently attached to the HBC synthon through an acetylene linker via Sonogashira-Hagihara cross-coupling from ethynyl-substituted HBC (Fig.…”