Synthesis and photoreactions of polyesters containing triazene and cinnamylidene malonyl units

Hoogen, N.; Nuyken, Oskar

doi:10.1002/(sici)1099-0518(20000515)38:10<1903::aid-pola780>3.0.co;2-q

Cited by 29 publications

(14 citation statements)

References 7 publications

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“…During the successive UV irradiation of polymer a decrease in intensity of the absorption was noted. This may be attributed to the dimerization of the olefinic double bond of the polymer chain, which involves the 2π + 2π cycloaddition reaction of the same leading to the formation of cyclobutane ring57 (Fig. 7).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene‐ether)esters containing α,β‐unsaturated ketone moiety in the main chain

Muthusamy

Krishnasamy

Murugavel

2013

J. Polym. Sci. A Polym. Chem.

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A series of poly(benzylidene-ether)esters containing a photoreactive benzylidene chromophore in the main chain were synthesized from 2,6-bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone (BHMBCH) with various aliphatic and aromatic diacid chlorides by an interfacial polycondensation technique. The intrinsic viscosity of the synthesized homo and copolymers determined by Ubbelohde viscometer was found to be 0.12 to 0.17 dL/g. The molecular structure of the monomer and polymers was confirmed by FT-IR, 1 H NMR, and 13 C NMR spectral analyses. These polymers were studied for their thermal stability and photochemical properties. Thermal properties were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). It was found that the polymers were stable up to 280 C and start degrading thereafter. Increase in acid methylene spacer length decreased the thermal stability. The self-extinguishing property of the synthe-sized polymers was studied by calculating the limiting oxygen index (LOI) value using a Van Krevelen's equation. The influence of the length of methylene spacer on phase transition was investigated using DSC and odd-even effect has been observed. Hot-stage optical polarizing microscopic (HOPM) study showed that most of the polymers exhibited birefringence and opalescence properties. The photolysis of liquid crystalline poly(benzylidene-ether)esters revealed that a,b-unsaturated ketone moiety in the main chain dimerises through 2p þ 2p cycloaddition reaction to form a cyclobutane derivative and leads to crosslinking.

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Section: Resultsmentioning

confidence: 99%

Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene‐ether)esters containing α,β‐unsaturated ketone moiety in the main chain

Muthusamy

Krishnasamy

Murugavel

2013

J. Polym. Sci. A Polym. Chem.

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“…On successive irradiation, the peak maximum decreased. This behavior clearly indicates the 2π + 2π cycloaddition of olefinic double bond leading to the formation of cyclobutane ring 29. The UV–Vis spectra representing the photocross‐linking behavior of the oligomers P3 and P7 are shown in Figures 11 and 12.…”

Section: Resultsmentioning

confidence: 94%

Synthesis, spectral, and thermal characterization of photoreactive epoxy resin containing cycloalkanone moiety in the main chain

Devi

Murugavel

2011

J of Applied Polymer Sci

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Dual functional epoxy resins were synthesized by solution polycondensation of 2,6-bis(4-hydroxy-3-methoxy benzylidene)cyclohexanone and 2,5-bis(4-hydroxy-3-methoxy benzylidene)cyclopentanone with epichlorohydrin. The synthesized epoxy resins were characterized systematically for their structure by UV, Fourier transform infrared (FTIR), 1 H NMR, and 13 C NMR spectroscopic techniques. Thermal characterization of synthesized epoxy resins was carried out by thermogravimetric analysis, and differential scanning calorimetry (DSC) under nitrogen atmosphere. The self extinguishing property of synthesized oligomers was studied by determining limiting oxygen index (LOI) values using Van Krevelen's equation. X-ray analysis showed that the epoxy resins containing cyclopentanone have higher degree of crystallinity. The photoreactive property of the synthesized epoxy resins in solution and film states was investigated by UV-Vis spectroscopy.The photocross-linking proceeds through the dimerization of olefinic chromophore present in the main chain of the oligomer via 2p þ 2p cycloaddition reaction. The influence of photoacid generator on the rate of photocross-linking of epoxy resin was studied by FTIR. UV irradiation of the epoxy resin in presence of photoacid generator produces aromatic sulfonium cation radicals and aromatic radicals which initiate the cationic ring-opening polymerization of oxirane ring. The photoreactivity studies of the oligomers by FTIR and DSC indicated the presence of dual functionality in the synthesized epoxy resins.

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“…Until now, different triazene polymers like polyesters, polysulphides, and polytriazenes have been reported in the literature. [5][6][7] In this regard, our contribution in the synthesis of novel triazene polyurethanes and copolyacrylates that combine the sensitivity of the triazene structure with an almost unlimited structural variability offered by the macromolecular chemistry of these polymers should be mentioned. [8][9][10][11] Moreover, in recent publications, the important attribute of the triazene copolymers to emit a strong fluorescence with a maximum around 400 nm was confirmed, feature of interest in chemosensor applications for the detection of some metal ions.…”

Section: Introductionmentioning

confidence: 99%

Preparation of amphiphilic block copolymer containing triazene moieties and fluorescence study

Buruiana¹,

Chibac²,

Melinte³

et al. 2013

J Chem Sci

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The present study describes the synthesis via microwave accelerated reversible additionfragmentation chain transfer (RAFT) polymerization of an amphiphilic block copolymer poly(acrylic acid)b-poly(dodecylacrylamide-co-1-(phenyl)-3-(2-methacryloyloxyethyl carbamoyloxyethyl)-3-methyltriazene-1) [PAA-b-(PDA-co-PUMA-T)]. The structure and the chemical composition of the block copolymer were confirmed by spectral/thermal analysis. The photoreactivity of the triazene sequences from PAA-b-(PDA-co-PUMA-T) was quantified by UV/vis irradiation in chloroform/dimethylformamide solutions and in thin film, indicating that the solvent polarity modifies with an order of magnitude the rate constant values. The lower rate constant in film state (k film = 1.3 × 10 −3 s −1 ), shows that the higher mobility of polymeric chains in solution allow a more rapid orientation, favourable to the triazene bond cleavage. The capability of block copolymer to form micelles in aqueous environment and implicitly, its critical micelle concentration (CMC) was evidenced through fluorescence measurements using pyrene probe (10 −6 M), the CMC value being of 4.64 × 10 −3 g L −1 PAA-b-(PDA-co-PUMA-T) (3.27 × 10 −7 M). Experiments of fluorescence quenching with various metal cations (UO 2+ 2 , Fe 2+ , Fe 3+ , Ni 2+ , Cu 2+ , Co 2+ , Pb 2+ and Hg 2+ ) suggested that such a block copolymer could find applications as fluorescence-based chemosensor for the detection of iron cations in homogeneous organic solutions or aqueous environments by thin films.

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Synthesis and photoreactions of polyesters containing triazene and cinnamylidene malonyl units

Cited by 29 publications

References 7 publications

Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene‐ether)esters containing α,β‐unsaturated ketone moiety in the main chain

Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene‐ether)esters containing α,β‐unsaturated ketone moiety in the main chain

Synthesis, spectral, and thermal characterization of photoreactive epoxy resin containing cycloalkanone moiety in the main chain

Preparation of amphiphilic block copolymer containing triazene moieties and fluorescence study

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