Controlled and selective placement of boron subphthalocyanines on either chain end of polymers synthesized by nitroxide mediated polymerization

Benoît H. Lessard; Timothy P. Bender; Benoît H. Lessard; Timothy P. Bender

doi:10.3934/molsci.2015.4.411

AIMS Molecular Science

2015, Volume 2, Issue 4: 411-426. doi: 10.3934/molsci.2015.4.411

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Controlled and selective placement of boron subphthalocyanines on either chain end of polymers synthesized by nitroxide mediated polymerization

Benoît H. Lessard ^{1,2
,
,},
Timothy P. Bender ^{2,3,4
,
,}

1.
Department of Chemical and Biological Engineering, University of Ottawa. 161 Louis Pasteur, Ottawa, Ontario, Canada K1N 6N5;
2.
Department of Chemical Engineering & Applied Chemistry University of Toronto. 200 College Street, Toronto, Ontario, Canada M5S 3E5;
3.
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada M5S 3H6;
4.
Department of Materials Science and Engineering, University of Toronto, 184 College St., Toronto, Ontario, Canada M5S 3E4

Received: 19 August 2015 Accepted: 08 October 2015 Published: 15 October 2015

In previous studies, we synthesized the first organic light emitting diode (OLED) using boron subphthalocyanines (BsubPcs) based polymers. When designing new polymer materials for organic electronic applications such as OLEDs or organic photovoltaic (OPV) devices it is important to consider not only the contribution of each monomer but also the polymer chain ends. In this paper we establish a post-polymerization strategy to couple BsubPcs onto either the α- or the ω-chain end using chemically selective BsubPc derivatives. We outline how the chain ends of two representative polymers, poly(styrene) (PS) and poly(n-butylacrylate) (BA), synthesized by nitroxide mediated polymerization (NMP), using BlocBuilder-MA as the initiating species, can be chemically modified by the incorporation of BsubPc chromophores. The addition of the BsubPc chromophore was confirmed through the use of a photodiode array detector (PDA) connected in-line with a gel permeation chromatography (GPC) setup. These findings represent the first reported method for the controlled and selective placement of a BsubPc chromophores on either end of a polymer produced by NMP. This strategy will therefore be utilized to make next generation BsubPc polymers for OLEDs and OPV devices. The extremely high molar extinction coefficient of BsubPc also make these polymers ideally suited for dye-labelling of polymers.
- boron subphthalocyanine (BsubPc),
- end-functional,
- nitroxide mediated polymerization (NMP)
Citation: Benoît H. Lessard, Timothy P. Bender. Controlled and selective placement of boron subphthalocyanines on either chain end of polymers synthesized by nitroxide mediated polymerization[J]. AIMS Molecular Science, 2015, 2(4): 411-426. doi: 10.3934/molsci.2015.4.411

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Abstract

In previous studies, we synthesized the first organic light emitting diode (OLED) using boron subphthalocyanines (BsubPcs) based polymers. When designing new polymer materials for organic electronic applications such as OLEDs or organic photovoltaic (OPV) devices it is important to consider not only the contribution of each monomer but also the polymer chain ends. In this paper we establish a post-polymerization strategy to couple BsubPcs onto either the α- or the ω-chain end using chemically selective BsubPc derivatives. We outline how the chain ends of two representative polymers, poly(styrene) (PS) and poly(n-butylacrylate) (BA), synthesized by nitroxide mediated polymerization (NMP), using BlocBuilder-MA as the initiating species, can be chemically modified by the incorporation of BsubPc chromophores. The addition of the BsubPc chromophore was confirmed through the use of a photodiode array detector (PDA) connected in-line with a gel permeation chromatography (GPC) setup. These findings represent the first reported method for the controlled and selective placement of a BsubPc chromophores on either end of a polymer produced by NMP. This strategy will therefore be utilized to make next generation BsubPc polymers for OLEDs and OPV devices. The extremely high molar extinction coefficient of BsubPc also make these polymers ideally suited for dye-labelling of polymers.

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