Preparation of polymers with pendant quinonoid groups and their photocrosslinking with visible light irradiation

Cha, Yong-Jun; Tsunooka, Masahiro; Tanaka, Makoto

doi:10.1002/app.1986.070310310

Cited by 9 publications

(5 citation statements)

References 16 publications

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“…In the same vein, polymers are now available with functional groups that are capable of crosslinking, e.g. light-activated quinonoid side chains (Cha et al, 1988). The design of polymers with pendant functional groups eliminates, in the former case, the need for the separate application and removal of excess surface coupling agents, and in the latter, the need for thorough mixing of monomer and cross-linker.…”

Section: Discussionmentioning

confidence: 99%

Cement precursor proteins of the reef-building polychaete Phragmatopoma californica (Fewkes)

Ra²,

De³

1992

Biochemistry

119

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Two distinctive 3,4-dihydroxyphenyl-L-alanine-(DOPA-) containing proteins (Pc-1 and Pc-2) have been isolated and partially characterized from the thorax of the reef-building sabellariid Phragmatopoma californica. They are the first such reported from the phylum Annelida. The proteins are presumed to be soluble precursors of the quinone-tanned cement used to bind particulate materials in the construction of the tubes that serve as habitats for the worms. The proteins have apparent molecular weights ranging from 18,000 to 20,000 and isoelectric point greater than or equal to 8.0. Both proteins consist of repeated sequence motifs in their primary structure. Pc-1 has repeats of (XGGY*GY*GAK) where X = V, L, I, AA, or KV, and Y* is DOPA or tyrosine. Pc-2, in contrast, appears to have repeats of (X1-[GGY*]n-[GA]m-X2-[HP(A)V]p-HK) where X1 can be AL, A, or F; X2 can be WG or absent; n and m can be 1 or 2, and p = 0-2. Both protein families appear to share the same C-terminal sequence ALGGY*GAGA. Of the DOPA-containing proteins characterized from other phyla, Phragmatopoma cement precursors most resemble those from the liver fluke Fasciola hepatica and the mussel Trichomya hirsuta.

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Section: Discussionmentioning

confidence: 99%

Cement precursor proteins of the reef-building polychaete Phragmatopoma californica (Fewkes)

Ra²,

De³

1992

Biochemistry

119

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“…Ethyl (7-coumaryloxy)acetate (2) was obtained as a white solid (10.627 g, 70.6%), mp 113-115 °C. JH NMR: 1.30 (t, 3 H, J = 7.5 Hz), 4.28 (q, 2 H, J = 7.5 Hz), 4.67 (s. 2 H), 6.26 (d, 1 H, J = 10 Hz), 6.77 (s, 1 H), 6.89 (d, 1 H, J = 9 Hz), 7.40 (d, 1 H, J = 9 Hz), 7.60 (d, 1 H, J = 10 Hz). IR (KBr): 3080, 2980, 2950, 1730, 1706, 1610, 1400, 1220, 1190, 1120, 1070, 980, 840 cm"1.…”

Section: Introductionmentioning

confidence: 99%

“…The analytical sample was recrystallized further from ethanol-benzene. 'H NMR (CDCla-DMSO-de): 4.73 (s, 2 ), 6.20 (d, 1 H, J = 10 Hz), 6.80 (s, 1 H), 6.92 (d, 1 H, J = 9 Hz), 7.48 (d, 1 H, J = 9 Hz), 7.80 (d, 1 H, J = 10 Hz), 12.79 (br s, 1 H). IR (KBr): 3080, 2980, 1720, 1610, 1400, 1240, 1220, 1120, 1070, 990, 830 cm-1.…”

Section: Introductionmentioning

confidence: 99%

Polyoxazoline having a coumarin moiety as a pendant group. Synthesis and photogelation

Chujo¹,

Sada²,

Saegusa³

1990

Macromolecules

129

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Polyoxazoline having a coumarin moiety in the pendant group was synthesized by the reaction of partially hydrolyzed poly(lV-acetylethylenimine) with (7-coumaryloxy)acetic acid in the presence of dicyclohexylcarbodiimide (DCC) as a condensing agent. The photosensitive polyoxazoline was irradiated with a 450-W high-pressure Hg lamp ( > 300 nm) for 7 h to produce polyoxazoline gels. These gels were swollen in water and showed characteristic properties of a hydrogel. Their equilibrium degree of swelling in water was controlled by the irradiation time and also by the degree of substitution of the coumarin moieties. The water uptake was up to 20 times the weight of the dry gel. The photocleavage reaction of the gel, which was monitored by its UV spectrum, was carried out by irradiation with a low-pressure Hg lamp ( ~253 nm).

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“…In addition, trans ‐cinnamate is reversibly isomerized to cis ‐cinnamate by irradiation at wavelengths longer than around 250 nm, and cis ‐cinnamate returns to trans ‐cinnamate by irradiation at around 250 nm. Photodimerization of alkyl cinnamates is a topic of ongoing interest, in part because of the potential use of alkyl cinnamates as photoresists with extensive applications in microlithography 73–76. Coumarinate exhibits a maximum absorption at around 310 nm, and irradiation of coumarinate at 300–350 nm generates dimers by cycloaddition similar to cinnamate [Scheme (B)] 77–80.…”

Section: Introductionmentioning

confidence: 99%

Photocycloaddition‐induced preparation of nanostructured, cyclic polymers using biscinnamated or biscoumarinated oligo(ethylene glycol)s

Nakayama

Matsuda

2005

J. Polym. Sci. A Polym. Chem.

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Two types of photoreactive water‐soluble oligo(ethylene glycol)s (OEGs; Mn = ca. 6500) were prepared by derivatization of OEG with photodimerizable groups such as cinnamates or coumarinates at both ends. Upon UV light irradiation of biscinnamated OEG in an aqueous solution, almost all trans‐cinnamate groups were isomerized to cis form in preference to dimerization even in an associated state at high concentrations of cinnamate groups, whereas dimerization via intermolecular photocycloaddition was the dominant process in methanol solution and in the film state. Coumarinate groups attached to OEG were photodimerized by UV irradiation, and this process was enhanced in an aqueous solution and in film cast from a polar solvent by hydrophobic association between coumarinate groups, resulting in the production of macromolecules. Kinetic analysis revealed that for low‐concentration aqueous solutions or a film cast from a nonpolar solvent, predominantly circular trimers to tetramers were produced on average, whereas from high‐concentration aqueous solutions or film cast from a polar solvent, mostly cyclic heptamers were produced. These results suggest that the molecular design of nanostructured, cyclic polymers of various sizes is possible by changing the concentration of aqueous solutions and cast solvents in this photoaddition system. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 3324–3336, 2005

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Preparation of polymers with pendant quinonoid groups and their photocrosslinking with visible light irradiation

Cited by 9 publications

References 16 publications

Cement precursor proteins of the reef-building polychaete Phragmatopoma californica (Fewkes)

Cement precursor proteins of the reef-building polychaete Phragmatopoma californica (Fewkes)

Polyoxazoline having a coumarin moiety as a pendant group. Synthesis and photogelation

Photocycloaddition‐induced preparation of nanostructured, cyclic polymers using biscinnamated or biscoumarinated oligo(ethylene glycol)s

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