Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives

Ceren Kutahya; Andrit Allushi; Recep Isci; Johannes Kreutzer; Turan Ozturk; Gorkem Yilmaz; Yusuf Yagci

doi:10.1021/acs.macromol.7b01335

Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives

Ceren Kutahya, Andrit Allushi, Recep Isci, Johannes Kreutzer, Turan Ozturk, Gorkem Yilmaz, Yusuf Yagci^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

68 Citations (Scopus)

Abstract

Photoinduced metal-free atom transfer radical polymerization (ATRP) activated by highly conjugated electron-rich thienothiophene derivatives, namely 4-[2-(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TT-TPA), 4-[2,5-bis(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TPA-TT-TPA), 4-(2-(4-(1,2,2-triphenylvinyl)phenyl) thieno[3,2-b]thiophen-3-yl)benzonitrile (TT-TPE) and 4-(2,5-bis(4-(1,2,2-triphenylvinyl)phenyl)thieno[3,2-b]thiophen-3- yl)benzonitrile (TPE-TT-TPE) is reported. Polymerization of methyl methacrylate (MMA) is efficiently activated and deactivated with light, forming polymers with controlled the molecular weight characteristics, dispersity, and chain end functionality. Polymerization studies and DFT calculations revealed that TT-TPA is the most efficient activator due to the favorable thermodynamic properties.

Original language	English
Pages (from-to)	6903-6910
Number of pages	8
Journal	Macromolecules
Volume	50
Issue number	17
DOIs	https://doi.org/10.1021/acs.macromol.7b01335
Publication status	Published - 12 Sept 2017

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© 2017 American Chemical Society.

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@article{28ca8316f1a04e33ad2f68cde4cefc6e,

title = "Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives",

abstract = "Photoinduced metal-free atom transfer radical polymerization (ATRP) activated by highly conjugated electron-rich thienothiophene derivatives, namely 4-[2-(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TT-TPA), 4-[2,5-bis(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TPA-TT-TPA), 4-(2-(4-(1,2,2-triphenylvinyl)phenyl) thieno[3,2-b]thiophen-3-yl)benzonitrile (TT-TPE) and 4-(2,5-bis(4-(1,2,2-triphenylvinyl)phenyl)thieno[3,2-b]thiophen-3- yl)benzonitrile (TPE-TT-TPE) is reported. Polymerization of methyl methacrylate (MMA) is efficiently activated and deactivated with light, forming polymers with controlled the molecular weight characteristics, dispersity, and chain end functionality. Polymerization studies and DFT calculations revealed that TT-TPA is the most efficient activator due to the favorable thermodynamic properties.",

author = "Ceren Kutahya and Andrit Allushi and Recep Isci and Johannes Kreutzer and Turan Ozturk and Gorkem Yilmaz and Yusuf Yagci",

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AU - Kutahya, Ceren

AU - Allushi, Andrit

AU - Isci, Recep

AU - Kreutzer, Johannes

AU - Ozturk, Turan

AU - Yilmaz, Gorkem

AU - Yagci, Yusuf

PY - 2017/9/12

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N2 - Photoinduced metal-free atom transfer radical polymerization (ATRP) activated by highly conjugated electron-rich thienothiophene derivatives, namely 4-[2-(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TT-TPA), 4-[2,5-bis(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TPA-TT-TPA), 4-(2-(4-(1,2,2-triphenylvinyl)phenyl) thieno[3,2-b]thiophen-3-yl)benzonitrile (TT-TPE) and 4-(2,5-bis(4-(1,2,2-triphenylvinyl)phenyl)thieno[3,2-b]thiophen-3- yl)benzonitrile (TPE-TT-TPE) is reported. Polymerization of methyl methacrylate (MMA) is efficiently activated and deactivated with light, forming polymers with controlled the molecular weight characteristics, dispersity, and chain end functionality. Polymerization studies and DFT calculations revealed that TT-TPA is the most efficient activator due to the favorable thermodynamic properties.

AB - Photoinduced metal-free atom transfer radical polymerization (ATRP) activated by highly conjugated electron-rich thienothiophene derivatives, namely 4-[2-(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TT-TPA), 4-[2,5-bis(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TPA-TT-TPA), 4-(2-(4-(1,2,2-triphenylvinyl)phenyl) thieno[3,2-b]thiophen-3-yl)benzonitrile (TT-TPE) and 4-(2,5-bis(4-(1,2,2-triphenylvinyl)phenyl)thieno[3,2-b]thiophen-3- yl)benzonitrile (TPE-TT-TPE) is reported. Polymerization of methyl methacrylate (MMA) is efficiently activated and deactivated with light, forming polymers with controlled the molecular weight characteristics, dispersity, and chain end functionality. Polymerization studies and DFT calculations revealed that TT-TPA is the most efficient activator due to the favorable thermodynamic properties.

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Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives

Abstract

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