Synthesis and Ring-Opening Metathesis Polymerization of o-Dialkoxy Paracyclophanedienes

Yurachat Janpatompong; Andrew M. Spring; Venukrishnan Komanduri; Raja U. Khan; Michael L. Turner

doi:10.1021/acs.macromol.2c02111

Synthesis and Ring-Opening Metathesis Polymerization of o-Dialkoxy Paracyclophanedienes

Yurachat Janpatompong, Andrew M. Spring, Venukrishnan Komanduri, Raja U. Khan, Michael L. Turner

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

Abstract

The highly strained ortho-diethylhexyloxy [2.2]paracyclophane-1,9-diene (M1) can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement. This paracyclophanediene undergoes ring-opening metathesis polymerization to give well-defined 2,3-dialkoxyphenylenevinylene polymers with an alternating cis/trans alkene stereochemistry and controllable molecular weight. Fully conjugated block copolymers with electron-rich and electron-deficient phenylene vinylene polymer segments can be prepared by sequential monomer additions. These polymers can be readily isomerized to the all-trans stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.

Original language	English
Pages (from-to)	10854-10864
Number of pages	11
Journal	Macromolecules
Volume	55
Issue number	24
DOIs	https://doi.org/10.1021/acs.macromol.2c02111
Publication status	Published - Dec 27 2022
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/acs.macromol.2c02111

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title = "Synthesis and Ring-Opening Metathesis Polymerization of o-Dialkoxy Paracyclophanedienes",

abstract = "The highly strained ortho-diethylhexyloxy [2.2]paracyclophane-1,9-diene (M1) can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement. This paracyclophanediene undergoes ring-opening metathesis polymerization to give well-defined 2,3-dialkoxyphenylenevinylene polymers with an alternating cis/trans alkene stereochemistry and controllable molecular weight. Fully conjugated block copolymers with electron-rich and electron-deficient phenylene vinylene polymer segments can be prepared by sequential monomer additions. These polymers can be readily isomerized to the all-trans stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.",

author = "Yurachat Janpatompong and Spring, {Andrew M.} and Venukrishnan Komanduri and Khan, {Raja U.} and Turner, {Michael L.}",

note = "Funding Information: The authors would like to thank the Development and Promotion of Science and Technology Talents Project (DPST), Thailand, for funding Y.J. V.K. acknowledges the financial support of the European Commission for the award of a Marie-Curie International Fellowship (CyclAr). The authors also thank Carlo Bawn for his technical advice. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

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doi = "10.1021/acs.macromol.2c02111",

language = "English",

volume = "55",

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publisher = "American Chemical Society",

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AU - Janpatompong, Yurachat

AU - Spring, Andrew M.

AU - Komanduri, Venukrishnan

AU - Khan, Raja U.

AU - Turner, Michael L.

N1 - Funding Information: The authors would like to thank the Development and Promotion of Science and Technology Talents Project (DPST), Thailand, for funding Y.J. V.K. acknowledges the financial support of the European Commission for the award of a Marie-Curie International Fellowship (CyclAr). The authors also thank Carlo Bawn for his technical advice. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/12/27

Y1 - 2022/12/27

N2 - The highly strained ortho-diethylhexyloxy [2.2]paracyclophane-1,9-diene (M1) can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement. This paracyclophanediene undergoes ring-opening metathesis polymerization to give well-defined 2,3-dialkoxyphenylenevinylene polymers with an alternating cis/trans alkene stereochemistry and controllable molecular weight. Fully conjugated block copolymers with electron-rich and electron-deficient phenylene vinylene polymer segments can be prepared by sequential monomer additions. These polymers can be readily isomerized to the all-trans stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.

AB - The highly strained ortho-diethylhexyloxy [2.2]paracyclophane-1,9-diene (M1) can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement. This paracyclophanediene undergoes ring-opening metathesis polymerization to give well-defined 2,3-dialkoxyphenylenevinylene polymers with an alternating cis/trans alkene stereochemistry and controllable molecular weight. Fully conjugated block copolymers with electron-rich and electron-deficient phenylene vinylene polymer segments can be prepared by sequential monomer additions. These polymers can be readily isomerized to the all-trans stereochemistry polymer. The optical and electrochemical properties of these polymers were investigated by theory and experiment.

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JF - Macromolecules

SN - 0024-9297

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ER -

Synthesis and Ring-Opening Metathesis Polymerization of o-Dialkoxy Paracyclophanedienes

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