Two different reaction mechanisms of cinnamate side groups attached to the various polymer backbones

Shi Joon Sung; Ki Yun Cho; Hyundae Hah; Jaemin Lee; Hong Ku Shim; Jung Ki Park

doi:10.1016/j.polymer.2006.02.003

Two different reaction mechanisms of cinnamate side groups attached to the various polymer backbones

Shi Joon Sung, Ki Yun Cho, Hyundae Hah, Jaemin Lee, Hong Ku Shim, Jung Ki Park

Division of Energy Techonology

Korea Advanced Institute of Science and Technology

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

Cinnamate polymers are well known photoreactive polymers due to [2+2] cycloaddition reaction of cinnamate side group. In this work, we have found that the cinnamate side groups could be also reacted by thermal energy, and this reaction is presumed to attribute to the radical reaction of carbon double bond in the cinnamate groups. Contrary to the photocycloaddition reaction of the cinnamate side groups, the thermal reaction of cinnamate side group was closely related to the flexibility of polymer backbone. The difference of the mechanism between the photocycloaddition reaction and thermal crosslinking reaction was confirmed by ¹H NMR and ¹³C NMR analysis of the model compound.

Original language	English
Pages (from-to)	2314-2321
Number of pages	8
Journal	Polymer
Volume	47
Issue number	7
DOIs	https://doi.org/10.1016/j.polymer.2006.02.003
State	Published - 22 Mar 2006

Bibliographical note

Funding Information:
This work was supported by the Center for Advanced Functional Polymers at KAIST.

Keywords

Cinnamate
Polymer flexibility
Thermal crosslinking

Access to Document

10.1016/j.polymer.2006.02.003

Cite this

@article{c13f957a437f43229c4c8bafcd65acd5,

title = "Two different reaction mechanisms of cinnamate side groups attached to the various polymer backbones",

abstract = "Cinnamate polymers are well known photoreactive polymers due to [2+2] cycloaddition reaction of cinnamate side group. In this work, we have found that the cinnamate side groups could be also reacted by thermal energy, and this reaction is presumed to attribute to the radical reaction of carbon double bond in the cinnamate groups. Contrary to the photocycloaddition reaction of the cinnamate side groups, the thermal reaction of cinnamate side group was closely related to the flexibility of polymer backbone. The difference of the mechanism between the photocycloaddition reaction and thermal crosslinking reaction was confirmed by 1H NMR and 13C NMR analysis of the model compound.",

keywords = "Cinnamate, Polymer flexibility, Thermal crosslinking",

author = "Sung, {Shi Joon} and Cho, {Ki Yun} and Hyundae Hah and Jaemin Lee and Shim, {Hong Ku} and Park, {Jung Ki}",

note = "Funding Information: This work was supported by the Center for Advanced Functional Polymers at KAIST. ",

year = "2006",

month = mar,

day = "22",

doi = "10.1016/j.polymer.2006.02.003",

language = "English",

volume = "47",

pages = "2314--2321",

journal = "Polymer",

issn = "0032-3861",

publisher = "Elsevier B.V.",

number = "7",

}

TY - JOUR

T1 - Two different reaction mechanisms of cinnamate side groups attached to the various polymer backbones

AU - Sung, Shi Joon

AU - Cho, Ki Yun

AU - Hah, Hyundae

AU - Lee, Jaemin

AU - Shim, Hong Ku

AU - Park, Jung Ki

N1 - Funding Information: This work was supported by the Center for Advanced Functional Polymers at KAIST.

PY - 2006/3/22

Y1 - 2006/3/22

N2 - Cinnamate polymers are well known photoreactive polymers due to [2+2] cycloaddition reaction of cinnamate side group. In this work, we have found that the cinnamate side groups could be also reacted by thermal energy, and this reaction is presumed to attribute to the radical reaction of carbon double bond in the cinnamate groups. Contrary to the photocycloaddition reaction of the cinnamate side groups, the thermal reaction of cinnamate side group was closely related to the flexibility of polymer backbone. The difference of the mechanism between the photocycloaddition reaction and thermal crosslinking reaction was confirmed by 1H NMR and 13C NMR analysis of the model compound.

AB - Cinnamate polymers are well known photoreactive polymers due to [2+2] cycloaddition reaction of cinnamate side group. In this work, we have found that the cinnamate side groups could be also reacted by thermal energy, and this reaction is presumed to attribute to the radical reaction of carbon double bond in the cinnamate groups. Contrary to the photocycloaddition reaction of the cinnamate side groups, the thermal reaction of cinnamate side group was closely related to the flexibility of polymer backbone. The difference of the mechanism between the photocycloaddition reaction and thermal crosslinking reaction was confirmed by 1H NMR and 13C NMR analysis of the model compound.

KW - Cinnamate

KW - Polymer flexibility

KW - Thermal crosslinking

UR - http://www.scopus.com/inward/record.url?scp=33644975967&partnerID=8YFLogxK

U2 - 10.1016/j.polymer.2006.02.003

DO - 10.1016/j.polymer.2006.02.003

M3 - Article

AN - SCOPUS:33644975967

SN - 0032-3861

VL - 47

SP - 2314

EP - 2321

JO - Polymer

JF - Polymer

IS - 7

ER -

Two different reaction mechanisms of cinnamate side groups attached to the various polymer backbones

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this