DOI: 10.1002/pola.20330. Click chemistry in materials synthesis. 1. Adhesive polymers from copper‐catalyzed azide‐alkyne cycloaddition

Click chemistry in materials synthesis. 1. Adhesive polymers from copper‐catalyzed azide‐alkyne cycloaddition

10.1002/pola.20330

Crossref journal-article

Wiley

Journal of Polymer Science Part A: Polymer Chemistry (311)

Abstract

AbstractThe copper(I)‐catalyzed cycloaddition reaction between azides and alkynes has been employed to make metal‐adhesive materials. Copper and brass surfaces supply the necessary catalytic Cu ions, and thus the polymerization process occurs selectively on these metals in the absence of added catalysts. Alternatively, copper compounds can be added to monomer mixtures and then introduced to reducing metal surfaces such as zinc to initiate polymerization. The resulting materials were found to possess comparable or superior adhesive strength to standard commercial glues, and structure‐activity correlations have identified several important properties of the monomers. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4392–4403, 2004

Bibliography

DÃaz, D. D., Punna, S., Holzer, P., McPherson, A. K., Sharpless, K. B., Fokin, V. V., & Finn, M. G. (2004). Click chemistry in materials synthesis. 1. Adhesive polymers from copperâcatalyzed azideâalkyne cycloaddition. Journal of Polymer Science Part A: Polymer Chemistry, 42(17), 4392â4403. Portico.

Authors 7

David D. Díaz (first)
Sreenivas Punna (additional)
Philipp Holzer (additional)
Andrew K. McPherson (additional)
K. Barry Sharpless (additional)
Valery V. Fokin (additional)
M. G. Finn (additional)

References 45 Referenced 394

10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
{'key': 'e_1_2_5_3_2', 'first-page': '1', 'volume-title': '1,3‐Dipolar Cycloaddition Chemistry', 'author': 'Huisgen R.', 'year': '1984'} / 1,3‐Dipolar Cycloaddition Chemistry by Huisgen R. (1984)
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
10.1021/ja021381e
10.1021/ja034490h
10.1021/ja036765z
10.1021/ja0370037
10.1021/ja0302836
10.1016/S1359-6446(03)02933-7
10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4
10.1002/anie.200352803
10.1021/ja020887u
10.1021/la0362977
10.1021/jp049601t
{'key': 'e_1_2_5_16_2', 'first-page': '115', 'volume': '41', 'author': 'Rogov N. G.', 'year': '1997', 'journal-title': 'Ross Khim Zh'} / Ross Khim Zh by Rogov N. G. (1997)
10.1021/jo011148j
10.1002/anie.200454078
10.1021/ja012672a
10.1021/ja001597l
10.1021/ja0015500
10.1021/jo981616y
10.1021/jm00078a008
10.1039/C39910001364
Preparation of (propargyloxy)benzene derivatives as fungicides: Place P.; Pepin R. (1987) FR patent 2598408 A1 1987113
Preparation of (propargyloxy)benzene derivatives as fungicides: Place P.; Pepin R. (1987) CAN 108:182220.
10.1021/ol006175v
{'key': 'e_1_2_5_27_2', 'first-page': '234', 'volume': '63', 'author': 'Korostova S. E.', 'year': '1990', 'journal-title': 'Zhurnal Prikladnoki Khimii'} / Zhurnal Prikladnoki Khimii by Korostova S. E. (1990)
10.1021/jo00119a057
10.1021/jo000734u
Experimental details are available from the authors upon request.
Fokin V. V. unpublished results.
10.1016/S0010-938X(01)00124-X
10.1021/la010575p
10.1023/A:1026725110344
10.1023/A:1004056527379
Lilyquist M. R.;Monsanto Corp; U.S. Pat. 3 318 728 19 670 509 1967.
10.1108/eb006943
10.1163/156856102320396175
10.1002/app.10837
Kent M. S. R.;Hurst M.;Small J.;Emerson J.;Zamora D.Sandia National Laboratories[Technical Report]1997 SAND97–10301.
Monomers were mixed in concentrated stock solutions using the minimum necessary amount of organic solvent (usually THF 0.5 M in each monomer). The required amount of stock mixture was then deposited at the center of each plate and the mixture was manually spread over the relevant region of the plate (previously marked in pencil) while the solvent evaporated. The two plates were then crossed at right angles to bring the treated surfaces in contact with each other and allowed to anneal under controlled conditions.
Measurements with the commercial adhesive most often tested in this work were less reproducible with an error of ±3 kg.
{'journal-title': 'Org Lett', 'year': '2004', 'author': 'Chan T. R.', 'key': 'e_1_2_5_43_2'} / Org Lett by Chan T. R. (2004)
{'volume-title': 'Principles of Polymer Chemistry', 'year': '1953', 'author': 'Flory P. J.', 'key': 'e_1_2_5_44_2'} / Principles of Polymer Chemistry by Flory P. J. (1953)
Preliminary experiments were also performed with extra large copper plates (surface contact area of 2 ×2 inches = 2581 mm2) and 100 mg of monomer mixtures. The most effective system supporting at least 25 kg in a peel test for at least 10 hours was composed of a 1.5:1 mixture of4and14(azide:alkyne ratio = 1:1).

Dates

Type	When
Created	21 years, 1 month ago (July 28, 2004, 4:01 p.m.)
Deposited	1 year, 11 months ago (Sept. 28, 2023, 10:55 a.m.)
Indexed	1 month, 3 weeks ago (July 14, 2025, 11:45 p.m.)
Issued	21 years, 1 month ago (July 28, 2004)
Published	21 years, 1 month ago (July 28, 2004)
Published Online	21 years, 1 month ago (July 28, 2004)
Published Print	21 years ago (Sept. 1, 2004)

Funders 8

National Institute of General Medical Sciences 10.13039/100000057
Region: Americas
gov (National government)
Labels2
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2. NIGMS
National Institutes of Health 10.13039/100000002
Region: Americas
gov (National government)
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1. Institutos Nacionales de la Salud
2. US National Institutes of Health
3. NIH
Awards1
1. GM 28,384
National Science Foundation
Awards1
1. CHE-9985553
W. M. Keck Foundation 10.13039/100000888
Region: Americas
pri (Trusts, charities, foundations (both public and private))
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1. Keck Foundation
2. The W. M. Keck Foundation
3. WMKF
The Skaggs Institute of Chemical Biology 10.13039/100011770 Skaggs Institute for Chemical Biology, Scripps Research Institute
Spanish MECD (Ministerio de Educación, Cultura y Desportes; Secretaría de Estado de Educación y Universidades)
Fondo Social Europeo 10.13039/501100004895 European Social Fund Plus
Region: Europe
gov (National government)
Labels58
1. Европейският социален фонд
2. Evropský sociální fond
3. Den Europæiske Socialfond
4. Europäischer Sozialfonds
5. Euroopa Sotsiaalfond
6. Ευρωπαϊκό Κοινωνικό Ταμείο
7. Fondo Social Europeo
8. Fonds social européen
9. Europski socijalni fond
10. Fondo sociale europeO
11. Eiropas Sociālais fonds
12. Europos socialinis fondas
13. Európai Szociális Alap
14. Fond Soċjali Ewropew
15. Europees Sociaal FondS
16. Europejski Fundusz Społeczny
17. Fundo Social Europeu
18. Fondul Social European
19. Európsky sociálny fond
20. Evropski socialni sklad
21. Euroopan sosiaalirahasto
22. Europeiska socialfonden
23. European Social Fund
24. Fondo Social Europeo Plus
25. Европейски социален фонд плюс
26. Evropský sociální fond plus
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31. Fonds social européen+
32. Europski socijalni fond plus
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37. Europees Sociaal Fonds Plus
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41. Európsky sociálny fond +
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Novartis Foundation 10.13039/100008273

BibTeX

@article{D_az_2004, title={Click chemistry in materials synthesis. 1. Adhesive polymers from copper‐catalyzed azide‐alkyne cycloaddition}, volume={42}, ISSN={1099-0518}, url={http://dx.doi.org/10.1002/pola.20330}, DOI={10.1002/pola.20330}, number={17}, journal={Journal of Polymer Science Part A: Polymer Chemistry}, publisher={Wiley}, author={Díaz, David D. and Punna, Sreenivas and Holzer, Philipp and McPherson, Andrew K. and Sharpless, K. Barry and Fokin, Valery V. and Finn, M. G.}, year={2004}, month=jul, pages={4392–4403} }

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