A route toward multifunctional polyurethanes using triple click reactions

Erhan Demirel; Hakan Durmaz; Gurkan Hizal; Umit Tunca

doi:10.1002/pola.27796

A route toward multifunctional polyurethanes using triple click reactions

Erhan Demirel, Hakan Durmaz, Gurkan Hizal, Umit Tunca^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

14 Citations (Scopus)

Abstract

The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH₂Cl₂ at room temperature for 10 days. Thereafter, the PU-(anthracene-co-alkyne-co-perfluorophenyl) (M_n,GPC = 15,400 g/mol, M_w/M_n= 1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels-Alder reactions, respectively, to finally yield PU-(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using ¹H NMR, GPC, and DSC.

Original language	English
Pages (from-to)	480-486
Number of pages	7
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	54
Issue number	4
DOIs	https://doi.org/10.1002/pola.27796
Publication status	Published - 15 Feb 2016

Bibliographical note

Publisher Copyright:
© 2015 Wiley Periodicals, Inc.

Keywords

active ester substitution
aliphatic polyurethane (PU)
alkyl amine
alkyne
anthracene
azide
CuAAC
Diels-Alder reaction
differential scanning calorimetry (DSC)
maleimide
NMR
perfluorophenyl ester
polycondensation
UV

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10.1002/pola.27796

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title = "A route toward multifunctional polyurethanes using triple click reactions",

abstract = "The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-(anthracene-co-alkyne-co-perfluorophenyl) (Mn,GPC = 15,400 g/mol, Mw/Mn= 1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels-Alder reactions, respectively, to finally yield PU-(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using 1H NMR, GPC, and DSC.",

keywords = "active ester substitution, aliphatic polyurethane (PU), alkyl amine, alkyne, anthracene, azide, CuAAC, Diels-Alder reaction, differential scanning calorimetry (DSC), maleimide, NMR, perfluorophenyl ester, polycondensation, UV",

author = "Erhan Demirel and Hakan Durmaz and Gurkan Hizal and Umit Tunca",

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AU - Demirel, Erhan

AU - Durmaz, Hakan

AU - Hizal, Gurkan

AU - Tunca, Umit

PY - 2016/2/15

Y1 - 2016/2/15

N2 - The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-(anthracene-co-alkyne-co-perfluorophenyl) (Mn,GPC = 15,400 g/mol, Mw/Mn= 1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels-Alder reactions, respectively, to finally yield PU-(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using 1H NMR, GPC, and DSC.

AB - The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-(anthracene-co-alkyne-co-perfluorophenyl) (Mn,GPC = 15,400 g/mol, Mw/Mn= 1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels-Alder reactions, respectively, to finally yield PU-(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using 1H NMR, GPC, and DSC.

KW - active ester substitution

KW - aliphatic polyurethane (PU)

KW - alkyl amine

KW - alkyne

KW - anthracene

KW - azide

KW - CuAAC

KW - Diels-Alder reaction

KW - differential scanning calorimetry (DSC)

KW - maleimide

KW - NMR

KW - perfluorophenyl ester

KW - polycondensation

KW - UV

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DO - 10.1002/pola.27796

M3 - Article

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SN - 0887-624X

VL - 54

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JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 4

ER -

A route toward multifunctional polyurethanes using triple click reactions

Abstract

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