Self-assembly and ring-opening metathesis polymerization of cyclic conjugated molecules on highly ordered pyrolytic graphite

Abstract

Cyclic conjugated monomers comprising cyclopentadithiophene-vinylene trimers and their polymers on HOPG are observed using STM and AFM. ROMP of the monomers is performed using a Grubbs catalyst. Their STM images exhibit single chains of planar polymers, whereas their AFM images show elongation of the polymer chains on HOPG.

Cyclic and linear dithienyl-anthryl vinylenes: synthesis, X-ray crystallography, spectroscopic properties, and photoinduced mechanical motions

“…[22][23][24][25][26][27] Recently, we have reported the synthesis and ROMP of various cyclophanedienes and cyclophanetrienes comprising bithiophene, cyclopentadithiophene, or benzothiadiazole. [28][29][30][31] These polymers obtained via ROMP formed microspheres to exhibit efficient whispering-gallery-mode photoluminescence (PL), showing potential application in microlasers. 29 Furthermore, cyclophanetriene with cyclophanediene and its polymers showed unique self-assembly and surface morphologies observed by scanning probe microscopy (STM) and atomic force microscopy (AFM).…”

“…29 Furthermore, cyclophanetriene with cyclophanediene and its polymers showed unique self-assembly and surface morphologies observed by scanning probe microscopy (STM) and atomic force microscopy (AFM). 30 Although they have such unique features, there is sporadic research on multifunctional cyclophanedienes or cyclophanetrienes due to the difficult synthesis of cyclic conjugated molecules. It is essential to link cyclic conjugated molecules with functional groups to discover new features.…”

Synthesis and electronic properties of pyridine end-capped cyclopentadithiophene-vinylene oligomers

“…Conversely to the case of the oligomers, the CPDTV unit monomer has been intensively used in co-polymer designs providing excellent solid-state eld effect transistor (FET) mobilities [4][5][6][7] and high performance in polymer-based organic solar cells. [8][9][10][11] Notable compounds in the family of p-conjugated oligomers based on nCPDTVs include the trimeric cyclic CPDTV 12,13 and the quinoidal tetracyano CPDTV compound. 1 We have also reported the unsubstituted series of nCPDTVs.…”

“…PynCPDTV by Wittig reaction between bisaldehydes 1a-d 1 and the ylides generated from 4-((triphenylphosphonio)methyl) pyridin-1-ium dichloride 2 21 and Bu t O À K + ; aer purication by column chromatography followed by GPC, PynCPDTV (3a-d) were obtained in 64-81% yield (see ESI le, Scheme S1, † for details). The chemical structures of all new compounds were veried by 1 H NMR, 13 C NMR, FT-IR and MALDI-TOF MS (for Experimental details and spectra see the ESI, Fig. S1-S27 †).…”

Conjugated Copolymers of Poly(arylenevinylene)s: Synthesis by Ring-Opening Metathesis Polymerization, Film Morphology, and Resonant Luminescence from Microspheres

“…Recently, we have reported the synthesis of a donor–acceptor conjugated copolymer of poly­(arylenevinylene)­s comprising electron-donating cyclopentadithiophene (CPDT) and accepting bis­(thienyl)­benzo­thiadiazole (DTBT) by ROMP of ring-strained cyclophanetrienes . In addition, the self-assembly and surface morphology of the CPDT monomers and homopolymers were studied . It is essential to conduct comprehensive studies on the synthesis of conjugated copolymers using new combinations of cyclic conjugated monomers, tailoring their spectroscopic properties and solid-state morphologies.…”