Novel Poly(phenylene vinylenes) with Well-Defined Poly(ε-caprolactone) or Polystyrene as Lateral Substituents:  Synthesis and Characterization

Colak, Demet Goen; Cianga, Ioan; Yaǧcı, Yusuf; Cirpan, and A.; Karasz, Frank E.

doi:10.1021/ma0703352

Cited by 28 publications

(23 citation statements)

References 55 publications

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“…two broad peaks with a long tail on low temperature region. The molecular weights of 3 and 4 are comparable (M n,GPC was determined as 28,320 for 3 and 32,000 for 4) and thus should have no significant effect on thermal stability [13]. The only difference is the presence of Br as substituent which should readily be lost during thermal degradation decreasing thermal stability.…”

Section: Resultsmentioning

confidence: 99%

“…The details of synthesis of PPV and initiators are given in our previous report [13]. Briefly, ring opening polymerization (ROP) of 3-caprolactone (CL) in the presence of the bifunctional initiator 2,5-dibromo-1,4-(dihydroxymethyl)benzene provided well defined low molecular weight polymers with dibromobenzene moieties.…”

Section: Synthesismentioning

confidence: 99%

“…In our recent studies we reported the syntheses and characterization of poly(phenylene)s and poly(phenylene vinylene)s with well defined poly(3-caprolactone) or polystyrene as lateral substituents by combination of the controlled polymerization methods atom transfer radical polymerization (ATRP) and ring opening polymerization (ROP), respectively, with Yamamoto, Suzuki [11,12] or Wittig polycondensation [13]. The resulting PPVs were soluble as were the starting macromonomers and showed blue or green fluorescence in solution [13].…”

Section: Introductionmentioning

confidence: 99%

“…The resulting PPVs were soluble as were the starting macromonomers and showed blue or green fluorescence in solution [13].…”

Section: Introductionmentioning

confidence: 99%

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Pyrolysis of poly(phenylene vinylene)s with polycaprolactone side chains

Nur¹,

Colak²,

Cianga³

et al. 2008

Polymer Degradation and Stability

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Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The resulting PPVs were soluble as were the starting macromonomers and showed blue or green fluorescence in solution [13].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pyrolysis of poly(phenylene vinylene)s with polycaprolactone side chains

Nur¹,

Colak²,

Cianga³

et al. 2008

Polymer Degradation and Stability

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“…This methodology affords possibility to incorporate functional groups into polyesters provided that in addition to the hydroxyl groups, the initiator contains desired functionality. Previously, we have prepared thermal- [21][22][23][24][25][26][27], photo- [28,29], and electro-functional [30] polymers of biocompatible polymers by taking advantage of the functional initiator approach [31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Küküt

Karal-Yılmaz

Yaǧcı

2012

Designed Monomers and Polymers

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In the present study, a new class of biodegradable graft copolymers of polystyrene (PS) with aliphatic polyester (APE) side chains were synthesized through combination of nitroxide-mediated free radical polymerization (NMRP) and ringopening polymerization (ROP) with copper (I)-catalyzed 'click' chemistry. First, the click component, azido-functional PS (PS-N 3 ) was prepared by copolymerization of styrene and chloromethyl styrene by NMRP followed by the conversion of chlorine groups of the resulting copolymer to azido groups by using NaN 3 in N,N-dimethylformamide. Propargyl functional APEs were prepared independently by ROP of lactic acid and glycolic acid using tin octoate in the presence of propargyl alcohol at 130°C. Finally, PS-N 3 was coupled with the resulting polymers by click chemistry to yield graft copolymers (PS-g-poly (L-lactic-co-glycolic acid) [PLLA] and PS-g-PLLGA, respectively). The intermediates and final graft copolymers were characterized by proton nuclear magnetic resonance ( 1 H NMR) and Fourier transform infrared spectral and gel permeation chromatography analyses. The hydrolytic degradation behavior of the obtained graft copolymers in phosphate buffer saline solution were investigated by the weight loss and molecular weight measurements. It is shown that both copolymers undergo slow hydrolytic degradation, PS-g-PGLLA being relatively faster due to the presence of hydrophilic glycolic acid groups in the structure.

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Synthesis of Well‐Defined Oligo(2,5‐dialkoxy‐1,4‐phenylene vinylene)s by Combined Olefin Metathesis and Wittig‐type Coupling: Effect of Conjugation Repeat Units and End Groups Toward Optical Properties

Abdellatif

Yorsaeng

Inagaki

et al. 2014

Macro Chemistry & Physics

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Defect-free, highly trans oligo(2,5-dialkoxy-1,4-phenylene vinylene)s [alkoxy = O(CH 2 ) 2 OSi i Pr 3 ] with both repeat units (ex. 9, 15, and 31 repeat units) and end groups (aldehyde, C 6 F 5 , terthiophene, ferrocene) well-defi ned are prepared by a stepwise combined olefi n metathesis using Mo(CHCMe 2 Ph)(N-2,6-Me 2 C 6 H 3 )[OCCH 3 (CF 3 ) 2 ] 2 with subsequent Wittig-type coupling. End-functionalized oligomers with uniform distributions are also prepared by acyclic diene metathesis (ADMET) condensation using a ruthenium-carbene catalyst, followed by the above combined olefi n metathesis and Wittig coupling. The effects of the repeat units and the end functional groups on the optical properties are explored; the photoluminescence quantum yields in the end-functionalized oligomers (e.g., 9 mers) are affected by the end groups. chemical purity, and supramolecular order. [ 2,3 ] We recently reported an exclusive synthesis of poly(9,9-di-n -octyl-fl uorene-2,7-vinylene)s (PFVs) containing oligo(thiophene)s in both chain ends, which exhibit unique emission properties due to an intramolecular energy transfer. [ 5d ] A facile, exclusive end functionalization can be achieved by treating the chain ends (vinyl groups) in the resultant PFVs, which were prepared by the acyclic diene metathesis (ADMET) polymerization using Ru-carbene catalyst, [5][6][7][8][9][10][11] with Mo(CHCMe 2 Ph)(N-2,6-Me 2 C 6 H 3 )[OCCH 3 (CF 3 ) 2 ] 2 ( Mo cat.) followed by Wittig-type coupling with certain aldehyde. [ 5,12,13 ] Moreover, the demonstrated ADMET method affords defect-free, stereoregular (all-trans ), high-molecularweight PFVs, [ 5 ] poly(2,5-dialkyl-phenylene-1,4-vinylene)s (PPVs) [ 6 ] containing well-defi ned chain ends, because the Scheme 1. Precise synthesis of all-trans oligo(2,5-dialkoxy-1,4-phenylene vinylene)s [ OPV s, alkoxy = O(CH 2 ) 2 OSi i Pr 3 ].Synthesis of Well-Defi ned Oligo(2,5-dialkoxy-1,4-phenylene vinylene)s . . .

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Novel Poly(phenylene vinylenes) with Well-Defined Poly(ε-caprolactone) or Polystyrene as Lateral Substituents: Synthesis and Characterization

Cited by 28 publications

References 55 publications

Pyrolysis of poly(phenylene vinylene)s with polycaprolactone side chains

Pyrolysis of poly(phenylene vinylene)s with polycaprolactone side chains

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Synthesis of Well‐Defined Oligo(2,5‐dialkoxy‐1,4‐phenylene vinylene)s by Combined Olefin Metathesis and Wittig‐type Coupling: Effect of Conjugation Repeat Units and End Groups Toward Optical Properties

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