2006
DOI: 10.1021/ma052451f
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Synthesis of a Novel Poly(iptycene) Ladder Polymer

Abstract: A self-polymerizable AB-type monomer for Diels−Alder (D−A) polymerization was prepared, and its polymerization was carried out in the melt phase and at high pressure in solution. The former method generated only low-molecular-weight polymer, but the latter one offered an efficient polymerization with increased molecular weight, due to the effect of high pressure on reactions with a negative activation volume. A pyridinium p-toluenesulfonate-catalyzed dehydration reaction of the D−A polymer led to a novel aroma… Show more

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Cited by 53 publications
(38 citation statements)
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References 58 publications
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“…In addition to the AA/BB-type monomers, selfpolymerizable AB-type monomers were also prepared. Swager et al [67] described the synthesis of 1,4-epoxy-5,12-dihexyloxy-1,4-dihydrotetracene, and its polymerization was carried out in the melt phase at high pressure in solution (Scheme 15). Additionally, a novel poly(iptycene) ladder polymer was successfully prepared via the dehydration Scheme 11 Synthetic route of main-chain LCPs [MP-m (m=2, 6, 10)] via Michael addition polymerization, and supramolecular hydrogen bonding interaction of these main-chain LCPs [61].…”
Section: Diels-alder Reactionmentioning
confidence: 99%
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“…In addition to the AA/BB-type monomers, selfpolymerizable AB-type monomers were also prepared. Swager et al [67] described the synthesis of 1,4-epoxy-5,12-dihexyloxy-1,4-dihydrotetracene, and its polymerization was carried out in the melt phase at high pressure in solution (Scheme 15). Additionally, a novel poly(iptycene) ladder polymer was successfully prepared via the dehydration Scheme 11 Synthetic route of main-chain LCPs [MP-m (m=2, 6, 10)] via Michael addition polymerization, and supramolecular hydrogen bonding interaction of these main-chain LCPs [61].…”
Section: Diels-alder Reactionmentioning
confidence: 99%
“…The Diels-Alder polymerization of AB-type monomers, and dehydration of the precursor polymer [67]. synthetic steps from inexpensive, commercially available reagents.…”
Section: Scheme 15mentioning
confidence: 99%
“…for 1 H and 39.50 p.p.m. for 13 C NMR) in DMSO-d 6 . Infrared (IR) spectra were recorded on a JASCO FT/IR-410 (JASCO, Tokyo, Japan).…”
Section: Measurementsmentioning
confidence: 99%
“…In contrast, defect-free ladder polymers have been synthesized using concerted reactions, particularly the Diels-Alder reaction. [3][4][5][6] In the course of our study of the controlled synthesis of N-substituted aromatic polyamides, 7,8 we have been interested in the synthesis and properties of aromatic ladder polyamides, in which two benzene rings are connected by two amide linkages. To synthesize this type of ladder polymer, we investigated the condensation reaction between N-alkylanthranilic acid methyl ester and N-alkylisatoic anhydride in the presence of a strong base, and developed a reaction that constructed two amide linkages successively between two benzene rings.…”
Section: Introductionmentioning
confidence: 99%
“…Generally, ladder polymers were synthesized by Diels-Alder reaction [5] of the two different monomers and stepwise cyclization of the linear polymers [6]. Furthermore, synthesized ladder polymers are often insoluble in common organic solvents due to that their conformational mobility is not flexible and gives entropic force for solubility.…”
Section: Introductionmentioning
confidence: 99%