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Volumn 41, Issue 11, 2008, Pages 3775-3778

Ionic dithioester-based RAFT agents derived from N-heterocyclic carbenes

Author keywords

[No Author keywords available]

Indexed keywords

CHAIN TRANSFER AGENTS (CTA); DITHIOESTER; FILTRATION TECHNIQUES; FUNCTIONALIZED; HIGH YIELDING; IMIDAZOLIUM; N HETEROCYCLIC CARBENES (NHC); N SUBSTITUTION; N-HETEROCYCLIC CARBENE (NHC); RADICAL POLYMERIZATIONS; RAFT AGENTS; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER (RAFT); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

EID: 45849146605     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma800241e     Document Type: Article
Times cited : (15)

References (48)
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    • For excellent reviews, see: a
    • For excellent reviews, see: (a) Lowe, A. B.; McCormick, C. L. Prog. Polym. Sci. 2007, 32, 283-351.
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    • For leading discussions of the mechanism of RAFT polymerizations, see: a
    • For leading discussions of the mechanism of RAFT polymerizations, see: (a) Moad, G.; Rizzardo, E.; Thang, S. H. Polymer 2008, 49, 1079-1131.
    • (2008) Polymer , vol.49 , pp. 1079-1131
    • Moad, G.1    Rizzardo, E.2    Thang, S.H.3
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    • For examples of cationic dithioester-based RAFT agents containing ammonium groups distal to their dithio moieties, see: (a) Baussard, J.-F, Habib-Jiwan, J.-L, Laschewsky, A, Mertoglu, M, Storsberg, J. Polymer 2004, 45, 3615-3626
    • For examples of cationic dithioester-based RAFT agents containing ammonium groups distal to their dithio moieties, see: (a) Baussard, J.-F.; Habib-Jiwan, J.-L.; Laschewsky, A.; Mertoglu, M.; Storsberg, J. Polymer 2004, 45, 3615-3626.
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    • For an example of a RAFT polymerization mediated by a quarternary dithiocarbamate, see
    • (c) Samakande, A.; Sanderson, R. D.; Hartmann, P. C. Synth. Commun. 2007, 37, 3861-3872. For an example of a RAFT polymerization mediated by a quarternary dithiocarbamate, see:
    • (2007) Synth. Commun , vol.37 , pp. 3861-3872
    • Samakande, A.1    Sanderson, R.D.2    Hartmann, P.C.3
  • 38
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    • For a report describing the utility of 2 in Suzuki-Miyaura coupling reactions, see: Tudose, A.; Delaude, L.; André, B.; Demonceau, A. Tetrahedron Lett. 2006, 47, 8529-8533.
    • For a report describing the utility of 2 in Suzuki-Miyaura coupling reactions, see: Tudose, A.; Delaude, L.; André, B.; Demonceau, A. Tetrahedron Lett. 2006, 47, 8529-8533.
  • 39
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    • The synthesis of 3 is similar to protocols used to prepare dithioester-based CTAs commonly used in RAFT polymerizations. See: Wood, M. R.; Duncalf, D. J.; Rannard, S. P.; Perrier, S. Org. Lett. 2006, 8, 553-556.
    • The synthesis of 3 is similar to protocols used to prepare dithioester-based CTAs commonly used in RAFT polymerizations. See: Wood, M. R.; Duncalf, D. J.; Rannard, S. P.; Perrier, S. Org. Lett. 2006, 8, 553-556.
  • 40
    • 45849142443 scopus 로고    scopus 로고
    • Rotational barriers were calculated at the Hartree-Fock 6-31G* level of theory, as implemented in the Spartan 2004 software package (Wavefunction, Inc., Irvine, CA 92612).
    • Rotational barriers were calculated at the Hartree-Fock 6-31G* level of theory, as implemented in the Spartan 2004 software package (Wavefunction, Inc., Irvine, CA 92612).
  • 41
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    • For examples of dithioester-based RAFT agents where the dithioester moiety is attached to the 1- or 5-position of an imidazole, see: (a) Carter, S, Rimmer, S, Sturdy, A, Webb, M. Macromol. Biosci. 2005, 5, 373-378
    • For examples of dithioester-based RAFT agents where the dithioester moiety is attached to the 1- or 5-position of an imidazole, see: (a) Carter, S.; Rimmer, S.; Sturdy, A.; Webb, M. Macromol. Biosci. 2005, 5, 373-378.
  • 44
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    • CTA ratios (up to 200:1). After 2 days at 110 °C, no polymer was observed when either 3 or 4 was used as the CTA
    • As controls, polymerizations were performed in the absence of AIBN using various styrene
    • As controls, polymerizations were performed in the absence of AIBN using various styrene:CTA ratios (up to 200:1). After 2 days at 110 °C, no polymer was observed when either 3 or 4 was used as the CTA. These results suggested to us that AIBN was essential for forming active radicals and hence polymer.
    • These results suggested to us that AIBN was essential for forming active radicals and hence polymer
  • 45
    • 45849105455 scopus 로고    scopus 로고
    • Molecular weights and polydispersities were determined using gel permeation chromatography (eluent = DMF/LiBr or THF) and are reported relative to polystyrene standards.
    • Molecular weights and polydispersities were determined using gel permeation chromatography (eluent = DMF/LiBr or THF) and are reported relative to polystyrene standards.
  • 46
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    • CTA.
    • CTA.
  • 47
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    • 3.
    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.