Relay Conjugation of Living Metathesis Polymers

Journal of the American Chemical Society
Liangbing FuWill R Gutekunst

Abstract

The covalent coupling of complex macromolecules is a modern challenge in both chemistry and biology. The development of efficient and chemoselective methods for polymer coupling and functionalization are increasingly important for designing new advanced materials and interfacing with biochemical systems. Herein, we present a new strategy to directly conjugate living polymers prepared using ring-opening metathesis polymerization (ROMP) to both small molecules and synthetic macromolecules. Central to this methodology is a terminal alkyne that serves as a directing group to promote a rapid, intramolecular reaction with an otherwise unreactive olefin. This highly chemoselective relay conjugation is compatible with a range of monomer families and uses a bench-stable enyne motif that can be easily introduced to functional targets. The rapid rate of the conjugation reaction paves the way for greatly streamlined construction of complex macromolecular systems derived from metathesis polymerization techniques without the need for specialized equipment.

References

Dec 13, 2001·Chemical Reviews·N HadjichristidisH Iatrou
Jul 6, 2002·Organic Letters·Robert M OwenLaura L Kiessling
Aug 19, 2004·Journal of the American Chemical Society·Thomas R HoyeHongyu Zhao
Aug 20, 2005·Science·Craig J Hawker, Karen L Wooley
Nov 13, 2007·Nature·Amir H Hoveyda, Adil R Zhugralin
Jul 24, 2008·Journal of the American Chemical Society·Stefan HilfAndreas F M Kilbinger
May 28, 2009·Journal of the American Chemical Society·Erin M KolonkoLaura L Kiessling
Jan 19, 2010·Journal of the American Chemical Society·Si Kyung YangMarcus Weck
Feb 18, 2010·Journal of Polymer Science. Part A, Polymer Chemistry·Zhou LiKaren L Wooley
Jun 24, 2010·Chemical Communications : Chem Comm·Sai Archana KroviSonBinh T Nguyen
Dec 7, 2010·Angewandte Chemie·Christopher Barner-KowollikWim Van Camp
Oct 1, 2009·Nature Chemistry·Stefan Hilf, Andreas F M Kilbinger
Apr 19, 2011·Macromolecules·Ahmad E MadkourGregory N Tew
Aug 9, 2011·Journal of the American Chemical Society·Claire F HansellRachel K O'Reilly
Sep 10, 2013·Polymer Chemistry·Jacquelin K KammeyerNathan C Gianneschi
Jul 2, 2014·Journal of the American Chemical Society·Eun-Hye KangTae-Lim Choi
Aug 1, 2014·Journal of the American Chemical Society·Carrie R JamesNathan C Gianneschi
Sep 23, 2014·Chemistry & Biology·Craig S McKay, M G Finn
Nov 18, 2014·Nature Materials·Isidro CoboSébastien Perrier
Apr 15, 2015·Accounts of Chemical Research·Guillaume DelaittreChristopher Barner-Kowollik
Jun 9, 2015·Journal of the American Chemical Society·Will R Gutekunst, Craig J Hawker
Jul 17, 2015·Advanced Materials·Cassandra E CallmannNathan C Gianneschi
May 25, 2016·Journal of the American Chemical Society·Scott C RadzinskiJohn B Matson
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Sep 26, 2017·Journal of the American Chemical Society·Dylan J WalshDamien Guironnet
Dec 7, 2017·Angewandte Chemie·Peng LiuAndreas F M Kilbinger
Feb 20, 2018·Journal of the American Chemical Society·Subhajit PalAndreas F M Kilbinger

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Citations

Dec 22, 2019·Angewandte Chemie·Noy B NechmadN Gabriel Lemcoff
Feb 13, 2021·Angewandte Chemie·Noy B NechmadN Gabriel Lemcoff
Jun 4, 2020·Macromolecules·Adam E LeviChristopher M Bates
Jul 15, 2020·Journal of the American Chemical Society·Xuelin SuiWill R Gutekunst

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