Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore

Chandra Kantha; Hansol Kim; Youngmee Kim; Jung Moo Heo; Joonyoung F. Joung; Sungnam Park; Jong Man Kim

doi:10.1016/j.dyepig.2018.02.039

Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore

Chandra Kantha, Hansol Kim, Youngmee Kim, Jung Moo Heo, Joonyoung F. Joung, Sungnam Park, Jong Man Kim

Department of Chemistry

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

20 Citations (Scopus)

Abstract

Tubular-shaped chromophores have great potential in chemical and material sciences. A naphthalene-containing macrocyclic diacetylene (MCDA-Naph) was synthesized to access covalently linked organic nanotubes (ONTs) through topochemical polymerization. Single crystal X-ray analysis revealed that MCDA-Naph adopts the desired tubular array with favorable molecular orientation. UV irradiation of the molecularly stacked MCDA-Naph resulted in 1,4-addition polymerization and the generation of conjugated ene-yne chromophores. Density functional theory (DFT) provided evidence for tubular polydiacetylene nanotubes.

Original language	English
Pages (from-to)	199-204
Number of pages	6
Journal	Dyes and Pigments
Volume	154
DOIs	https://doi.org/10.1016/j.dyepig.2018.02.039
Publication status	Published - 2018 Jul

Keywords

Chromophore
Conjugated polymer
Macrocyclic diacetylene
Polydiacetylene
Topochemical polymerization

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

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10.1016/j.dyepig.2018.02.039

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title = "Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore",

abstract = "Tubular-shaped chromophores have great potential in chemical and material sciences. A naphthalene-containing macrocyclic diacetylene (MCDA-Naph) was synthesized to access covalently linked organic nanotubes (ONTs) through topochemical polymerization. Single crystal X-ray analysis revealed that MCDA-Naph adopts the desired tubular array with favorable molecular orientation. UV irradiation of the molecularly stacked MCDA-Naph resulted in 1,4-addition polymerization and the generation of conjugated ene-yne chromophores. Density functional theory (DFT) provided evidence for tubular polydiacetylene nanotubes.",

keywords = "Chromophore, Conjugated polymer, Macrocyclic diacetylene, Polydiacetylene, Topochemical polymerization",

author = "Chandra Kantha and Hansol Kim and Youngmee Kim and Heo, {Jung Moo} and Joung, {Joonyoung F.} and Sungnam Park and Kim, {Jong Man}",

note = "Funding Information: This study was supported by the Samsung Research Funding Center of Samsung Electronics (Project Number SRFC-MA1501-06 ) and the National Research Foundation of Korea ( NRF-2017R1A2A1A05000752 ). Publisher Copyright: {\textcopyright} 2018 Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "2018",

month = jul,

doi = "10.1016/j.dyepig.2018.02.039",

language = "English",

volume = "154",

pages = "199--204",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

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TY - JOUR

T1 - Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore

AU - Kantha, Chandra

AU - Kim, Hansol

AU - Kim, Youngmee

AU - Heo, Jung Moo

AU - Joung, Joonyoung F.

AU - Park, Sungnam

AU - Kim, Jong Man

N1 - Funding Information: This study was supported by the Samsung Research Funding Center of Samsung Electronics (Project Number SRFC-MA1501-06 ) and the National Research Foundation of Korea ( NRF-2017R1A2A1A05000752 ). Publisher Copyright: © 2018 Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/7

Y1 - 2018/7

N2 - Tubular-shaped chromophores have great potential in chemical and material sciences. A naphthalene-containing macrocyclic diacetylene (MCDA-Naph) was synthesized to access covalently linked organic nanotubes (ONTs) through topochemical polymerization. Single crystal X-ray analysis revealed that MCDA-Naph adopts the desired tubular array with favorable molecular orientation. UV irradiation of the molecularly stacked MCDA-Naph resulted in 1,4-addition polymerization and the generation of conjugated ene-yne chromophores. Density functional theory (DFT) provided evidence for tubular polydiacetylene nanotubes.

AB - Tubular-shaped chromophores have great potential in chemical and material sciences. A naphthalene-containing macrocyclic diacetylene (MCDA-Naph) was synthesized to access covalently linked organic nanotubes (ONTs) through topochemical polymerization. Single crystal X-ray analysis revealed that MCDA-Naph adopts the desired tubular array with favorable molecular orientation. UV irradiation of the molecularly stacked MCDA-Naph resulted in 1,4-addition polymerization and the generation of conjugated ene-yne chromophores. Density functional theory (DFT) provided evidence for tubular polydiacetylene nanotubes.

KW - Chromophore

KW - Conjugated polymer

KW - Macrocyclic diacetylene

KW - Polydiacetylene

KW - Topochemical polymerization

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U2 - 10.1016/j.dyepig.2018.02.039

DO - 10.1016/j.dyepig.2018.02.039

M3 - Article

AN - SCOPUS:85042940458

SN - 0143-7208

VL - 154

SP - 199

EP - 204

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore

Abstract

Keywords

ASJC Scopus subject areas

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