Acetylene-functionalized lithium initiators for anionic polymerization. Powerful precursors for "click" chemistry

Athanasios Touris; Jimmy W. Mays; Nikos Hadjichristidis

doi:10.1021/ma102881m

Acetylene-functionalized lithium initiators for anionic polymerization. Powerful precursors for "click" chemistry

Athanasios Touris, Jimmy W. Mays, Nikos Hadjichristidis^*

^*Corresponding author for this work

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

10 Scopus citations

Abstract

Two novel anionic acetylene-functionalized initiators, 5-trimethylsilyl-4- pentynyllithium (TMSPLi) and 5-triethylsilyl-4-pentynyllithium (TESPLi), were synthesized and characterized by ¹H NMR, ¹³C NMR, and GC-MS. TMSPLi was successfully used for the polymerization of styrene, but not for the polymerization of isoprene and butadiene. On the other hand, TESPLi exhibited all characteristics of an anionic initiator for the (co)polymerization of styrene, isoprene, and butadiene. TESPLi is ideal for the synthesis of living well-defined (co)polymers with acetylene end groups, perfect candidates for "click" reactions and at the same time possessing all the potential of living anionic polymerization for the synthesis of well-defined complex macromolecular architectures.

Original language	English (US)
Pages (from-to)	1886-1893
Number of pages	8
Journal	Macromolecules
Volume	44
Issue number	7
DOIs	https://doi.org/10.1021/ma102881m
State	Published - Apr 12 2011
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Acetylene-functionalized lithium initiators for anionic polymerization. Powerful precursors for {"}click{"} chemistry",

abstract = "Two novel anionic acetylene-functionalized initiators, 5-trimethylsilyl-4- pentynyllithium (TMSPLi) and 5-triethylsilyl-4-pentynyllithium (TESPLi), were synthesized and characterized by 1H NMR, 13C NMR, and GC-MS. TMSPLi was successfully used for the polymerization of styrene, but not for the polymerization of isoprene and butadiene. On the other hand, TESPLi exhibited all characteristics of an anionic initiator for the (co)polymerization of styrene, isoprene, and butadiene. TESPLi is ideal for the synthesis of living well-defined (co)polymers with acetylene end groups, perfect candidates for {"}click{"} reactions and at the same time possessing all the potential of living anionic polymerization for the synthesis of well-defined complex macromolecular architectures.",

author = "Athanasios Touris and Mays, {Jimmy W.} and Nikos Hadjichristidis",

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T1 - Acetylene-functionalized lithium initiators for anionic polymerization. Powerful precursors for "click" chemistry

AU - Touris, Athanasios

AU - Mays, Jimmy W.

AU - Hadjichristidis, Nikos

PY - 2011/4/12

Y1 - 2011/4/12

N2 - Two novel anionic acetylene-functionalized initiators, 5-trimethylsilyl-4- pentynyllithium (TMSPLi) and 5-triethylsilyl-4-pentynyllithium (TESPLi), were synthesized and characterized by 1H NMR, 13C NMR, and GC-MS. TMSPLi was successfully used for the polymerization of styrene, but not for the polymerization of isoprene and butadiene. On the other hand, TESPLi exhibited all characteristics of an anionic initiator for the (co)polymerization of styrene, isoprene, and butadiene. TESPLi is ideal for the synthesis of living well-defined (co)polymers with acetylene end groups, perfect candidates for "click" reactions and at the same time possessing all the potential of living anionic polymerization for the synthesis of well-defined complex macromolecular architectures.

AB - Two novel anionic acetylene-functionalized initiators, 5-trimethylsilyl-4- pentynyllithium (TMSPLi) and 5-triethylsilyl-4-pentynyllithium (TESPLi), were synthesized and characterized by 1H NMR, 13C NMR, and GC-MS. TMSPLi was successfully used for the polymerization of styrene, but not for the polymerization of isoprene and butadiene. On the other hand, TESPLi exhibited all characteristics of an anionic initiator for the (co)polymerization of styrene, isoprene, and butadiene. TESPLi is ideal for the synthesis of living well-defined (co)polymers with acetylene end groups, perfect candidates for "click" reactions and at the same time possessing all the potential of living anionic polymerization for the synthesis of well-defined complex macromolecular architectures.

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Acetylene-functionalized lithium initiators for anionic polymerization. Powerful precursors for "click" chemistry

Abstract

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