Living cationic polymerization of N-vinylcarbazole initiated by hydrogen iodide

Sawamoto, Mitsuo; Fujimori, Junichi; Higashimura, Toshinobu

doi:10.1021/ma00171a003

Cited by 102 publications

(60 citation statements)

References 3 publications

(4 reference statements)

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“…Recent developments in this field are mostly connected to the applications in polymeric‐light emitting diodes, organic photorefractive materials, and photovoltaic devices. A strong basic monomer, NVC, undergoes facile cationic polymerization with almost all cationic initiators to give poly(NVC), and the living cationic polymerization of NVC with hydrogen iodide was also reported 2. Free radical initiators, such as azo compounds and peroxides, readily polymerize NVC, and radical polymerization was used in manufacturing the polymer 1…”

Section: Introductionmentioning

confidence: 98%

Xanthate‐Mediated Controlled Radical Polymerization of N‐Vinylcarbazole

Mori

Ookuma

Nakano

et al. 2006

Macro Chemistry & Physics

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Summary: Well‐defined poly(N‐vinylcarbazole) [poly(NVC)] was synthesized by macromolecular design via interchange of the xanthates (MADIX)/reversible addition‐fragmentation chain transfer (RAFT) polymerization. The homopolymers with controlled molecular weights ($\overline M _{\rm n}$ = 3 000–48 000) and low polydispersities indices ($\overline M _{\rm w} /\overline M _{\rm n}$ = 1.15–1.20) were obtained by the polymerization of NVC with AIBN in the presence of O‐ethyl‐S‐(1‐phenylethyl) dithiocarbonate as a xanthate‐type chain transfer agent (CTA). Good control of the polymerization was confirmed by the linear first‐order kinetic plot, the molecular weight controlled by the monomer/CTA molar ratio, linear increase in the molecular weight with the conversion, and the ability to extend the chains by the second addition of the monomer.Radical polymerization of NVC in the presence of CTA and plot of number‐average molecular weight (circles) and polydispersity (squares) as a function of conversion.magnified imageRadical polymerization of NVC in the presence of CTA and plot of number‐average molecular weight (circles) and polydispersity (squares) as a function of conversion.

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Section: Introductionmentioning

confidence: 98%

Xanthate‐Mediated Controlled Radical Polymerization of N‐Vinylcarbazole

Mori

Ookuma

Nakano

et al. 2006

Macro Chemistry & Physics

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“…[80][81][82] The highest the acidity (low pK a ), the most reactive initiator is the Brö nsted acid. Strong nucleophilic counteranions react with the carbocation, leading to the formation of the nonpropagating covalent compounds (Scheme 7).…”

Section: Brönsted Acidsmentioning

confidence: 99%

Ionic Polymerization

Pitsikalis

2013

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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“…In the case of PVCz, living cationic polymerizations using hydrogen iodide as an initiator have been used to produce well-defined polymers with narrow molecular weight distributions (M w =M n ¼ 1.2-1.3). [9] Anionic polymerizations have also been attempted but the molecular weight distributions are relatively broad with polydispersity indices (PDIs) %2-10. [10] More recently, the development of controlled or living radical polymerization methods avoids these exhaustive procedures, particularly functional group protection, while approaching the control over molecular weight distribution and microstructure exhibited by polymers made by ionic polymerizations.…”

Section: Full Papermentioning

confidence: 99%

Synthesis of Hydroxyl‐Terminated Poly(vinylcarbazole‐ran‐styrene) Copolymers by Nitroxide‐Mediated Polymerization

Morton

Graffe

Marić

2007

Macro Chemistry & Physics

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A series of poly(vinylcarbazole‐ran‐styrene) copolymers with terminal hydroxyl groups were synthesized using nitroxide mediated polymerization (NMP) with the hydroxyl‐functional initiator VA‐086 and TEMPO as the mediator at 130 °C. Polymerizations were studied as a function of vinylcarbazole feed content, target molecular weight, and VA‐086/TEMPO ratio. The characterization of the copolymers was done by GPC and NMR. For feed concentrations of 40 mol‐% vinylcarbazole, copolymers with vinylcarbazole concentration up to 33 mol‐% could be obtained with narrow molecular weight distributions (PDI = 1.35) and exhibit pseudo‐“living” character up to conversions of about 20% if the target molecular weight was >100 kg · mol−1. 1H NMR indicated that the hydroxyl group was retained sufficiently with a functionality typically of about 0.7 hydroxyl groups per chain. Copolymers synthesized with higher vinylcarbazole feed content exhibited slower kinetics and were less controlled, resulting in much broader molecular weight distributions. The absence of control could be attributed to the absence of thermal initiation by vinylcarbazole which is advantageous toward controlling the radical concentration during the polymerization.magnified image

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Living cationic polymerization of N-vinylcarbazole initiated by hydrogen iodide

Cited by 102 publications

References 3 publications

Xanthate‐Mediated Controlled Radical Polymerization of N‐Vinylcarbazole

Xanthate‐Mediated Controlled Radical Polymerization of N‐Vinylcarbazole

Ionic Polymerization

Synthesis of Hydroxyl‐Terminated Poly(vinylcarbazole‐ran‐styrene) Copolymers by Nitroxide‐Mediated Polymerization

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