Hostname: page-component-78c5997874-fbnjt Total loading time: 0 Render date: 2024-11-16T19:18:38.913Z Has data issue: false hasContentIssue false
  • English
  • Français

Synthesis and Processing of Organic Materials in Supercritical Carbon Dioxide

Published online by Cambridge University Press:  31 January 2011

Georgia E. McCluskey ,
Jin-Kyun Lee ,
Jing Sha ,
Christopher K. Ober ,
Scott E. Watkins  and
Andrew B. Holmes
Get access

Abstract

Carbon dioxide (CO2) is arguably the most high-profile molecule of recent times. Although much of its bad press comes from environmental concerns associated with greenhouse gas emissions, there exists the possibility to harness this abundant resource for application to the synthesis and processing of useful materials. This article describes a selection of recent successes in using supercritical carbon dioxide (scCO2) as a solvent for polymerizations. Further, the uses of compressed CO2 as a processing tool in the fabrication of materials for applications such as coatings and biomaterials are discussed. Finally, the application of scCO2 to photolithography is demonstrated, with particular focus on CO2 as a processing solvent for the patterning of organic electronic devices.

Type
Research Article
Information
MRS Bulletin , Volume 34 , Issue 2: Exploiting New Opportunities in Materials Research by Remembering and Applying Old Lessons , February 2009 , pp. 108 - 115
Copyright
Copyright © Materials Research Society 2009

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1Poliakoff, M., Fitzpatrick, M.J., Farren, T.R., Anastas, P.T., Science 297, 807 (2002).CrossRefGoogle ScholarPubMed
2Beckman, E.J., J. Supercrit. Fluids 28, 121 (2004).CrossRefGoogle Scholar
3Ritter, S.K., Chem. Eng. News 85, 11 (2007).Google Scholar
4Leitner, W., Appl. Organomet. Chem. 14, 809 (2000).3.0.CO;2-#>CrossRefGoogle Scholar
5Wells, S.L., DeSimone, J., Angew. Chem., Int. Ed. 40, 518 (2001).3.0.CO;2-4>CrossRefGoogle Scholar
6Zhang, X.G., Johnson, K.P., Chin. Sci. Bull. 52, 27 (2007).CrossRefGoogle Scholar
7Cooper, A.I., Londono, J.D., Wignall, G., McClain, J.B., Samulski, E.T., Lin, J.S., Dobrynin, A., Rubenstein, M., Burke, A.L.C., Fréchet, J.M.J., DeSimone, J.M., Nature 389, 368 (1997).CrossRefGoogle Scholar
8Rayner, C.M., Org. Process Res. Dev. 11, 121 (2007).CrossRefGoogle Scholar
9Mikami, K., Green Reaction Media in Organic Synthesis (Blackwell, Oxford, U.K., 2005).CrossRefGoogle Scholar
10Leitner, W., Acc. Chem. Res. 35, 746 (2002).CrossRefGoogle Scholar
11Jessop, P.G., Leitner, W., Chemical Synthesis Using Supercritical Fluids (Wiley, New York, 1999).CrossRefGoogle Scholar
12DeSimone, J.M., Guan, Z., Elsbern, C.S., Science 257, 945 (1992).CrossRefGoogle Scholar
13Bray, C.L., Tan, B., Wood, C.D., Cooper, A.I., J. Mater. Chem. 15, 456 (2005).CrossRefGoogle Scholar
14Tan, B., Woods, H.M., Licence, P., Howdle, S.M., Cooper, A.I., Macromolecules 38, 1691 (2005).CrossRefGoogle Scholar
15Sarbu, T., Styranec, T., Beckman, E.J., Nature 405, 165 (2000).CrossRefGoogle Scholar
16Tsukahara, T., Kayaki, Y., Ikariya, T., Ikeda, Y., Angew. Chem., Int. Ed. 43, 3719 (2004).CrossRefGoogle Scholar
17Kendall, J.L., Canelas, D.A., Young, J.L., DeSimone, J.M., Chem. Rev. 99, 543 (1999).CrossRefGoogle Scholar
18Cooper, A.I., J. Mater. Chem. 10, 207 (2000).CrossRefGoogle Scholar
19McCoy, M., Chem. Eng. News 77, 10 (1999).Google Scholar
20Wood, C.D., Cooper, A.I., DeSimone, J.M., Curr. Opin. Solid State Mater. Sci. 8, 325 (2004).CrossRefGoogle Scholar
21www.teflon.com (accessed June 4, 2008).Google Scholar
22Ahmed, T.S., DeSimone, J.M., Roberts, G.W., Macromolecules 40, 9322 (2007).CrossRefGoogle Scholar
23Gregory, A.M., Thurecht, K.J., Howdle, S.M., Macromolecules 41, 1215 (2008).CrossRefGoogle Scholar
24Villarroya, S., Zhou, J., Duxbury, C.J., Heis, A., Howdle, S.M., Macromolecules 39, 633 (2006).CrossRefGoogle Scholar
25Arakawa, H., Aresta, M., Armor, J., Barteau, M., Beckman, E., Bell, A., Bercaw, J., Creutz, C., Dixon, D.A., Dixon, D., Domen, K., DuBois, D., Eckert, J., Fujita, E., Gibson, D., Goddard, W., Goodman, D., Keller, J., Kubas, G., Kung, H., Lyons, J., Manzer, L., Marks, T., Morokuma, K., Nicholas, K., Periana, R., Que, L., Rostrup-Nielson, J., Sachtler, W., Schmidt, L., Sen, A., Somorjai, G., Stair, P., Stults, B., Tumas, W., Chem. Rev. 101, 953 (2001).CrossRefGoogle Scholar
26Lu, X.-B., Wang, Y., Angew. Chem., Int. Ed. 43, 3574 (2004).CrossRefGoogle Scholar
27Inoue, S., Koinuma, H., Tsuruta, T., J. Polym. Sci. C: Polym. Lett. 7, 287 (1969).Google Scholar
28Stamp, L.M., Mang, S.A., Holmes, A.B., Knights, K.A., Miguel, Y.R.D., McConvey, I.F., Chem. Commun. 23, 2502 (2001).CrossRefGoogle Scholar
29Mang, S., Cooper, A.I., Colclough, M.E., Chauhan, N., Holmes, A.B., Macromolecules 33, 303 (2000).CrossRefGoogle Scholar
30Cohen, C.T., Coates, G.W., J. Polym. Sci. A: Polym. Chem. 44, 5182 (2006).CrossRefGoogle Scholar
31Robertson, N.J., Qin, Z., Dallinger, G.C., Lobkovsky, E.B., Lee, S., Coates, G.W., Dalton Trans. 5390 (2006).CrossRefGoogle Scholar
32Hoy, K.L., Nielson, K.A., Chem. Abstr. 112:218843, EP 350909 (1990).Google Scholar
33Hoy, K.L., Nielson, K.A., Chinsoo, L., Chem. Abstr. 112:218842, EP 350910 (1990).Google Scholar
34Hay, J.N., Khan, A., J. Mater. Sci. 37, 4743 (2002).CrossRefGoogle Scholar
35Davies, O.R., Lewis, A.L., Whitaker, M.J., Tai, H., Shakesheff, K.M., Howdle, S.M., Adv. Drug Delivery Rev. 60, 373 (2008).CrossRefGoogle Scholar
36Tai, H., Popov, V.K., Shakesheff, K.M., Howdle, S.M., Biochem. Soc. Trans. 35, 516 (2007).CrossRefGoogle Scholar
37Tan, B., Lee, J.-Y., Cooper, A.I., Macromolecules 40, 1945 (2007).CrossRefGoogle Scholar
38Lee, J.-Y., Tan, B., Cooper, A.I., Macromolecules 40, 1955 (2007).CrossRefGoogle Scholar
39Cooper, A.I., Adv. Mater. 13, 1111 (2001).3.0.CO;2-L>CrossRefGoogle Scholar
40Weibel, G.L., Ober, C.K., Microelectron. Eng. 65, 145 (2003).CrossRefGoogle Scholar
41Jones, C.A., Zweber, A., DeYoung, J.P., McClain, J.B., Carbonell, R., DeSimone, J.M., Crit. Rev. Solid State Mater. Sci. 29, 97 (2004).CrossRefGoogle Scholar
42Williams, E.D., Ayres, R.U., Heller, M., Environ. Sci. Technol. 36, 5504 (2002).CrossRefGoogle Scholar
43Thompson, L.F., Introduction to Microlithography (American Chemical Society, Washington, DC, ed. 2, 1998).Google Scholar
44Ito, H., Adv. Polym. Sci. 172, 37 (2005).CrossRefGoogle Scholar
45Hoggan, E.N., Flowers, D., Wang, K., DeSimone, J.M., Carbonell, R.G., Ind. Eng. Chem. Res. 43, 2113 (2004).CrossRefGoogle Scholar
46Ober, C.K., Gabor, A.H., Gallagher-Wetmore, P., Allen, R.D., Adv. Mater. 9, 1039 (1997).CrossRefGoogle Scholar
47Boggiano, M.K., Vellenga, D., Carbonell, R., Ashby, V.S., DeSimone, J.M., Polymer 47, 4012 (2006).CrossRefGoogle Scholar
48Sundararajan, N., Yang, S., Ogino, K., Valiyaveettil, S., Wang, J.-G., Zhou, X., Ober, C.K., Obendorf, S.K., Allen, R.D., Chem. Mater. 12, 41 (2000).CrossRefGoogle Scholar
49Pham, V.Q., Ferris, R.J., Hamad, A., Ober, C.K., Chem. Mater. 15, 4893 (2003).CrossRefGoogle Scholar
50Yang, S., Wang, J., Ogino, K., Valiyaveettil, S., Ober, C.K., Chem. Mater. 12, 33 (2000).CrossRefGoogle Scholar
51Hoggan, E.N., Wang, K., Flowers, D., DeSimone, J.M., Carbonell, R.G., IEEE Trans. Semicond. Manuf. 17, 510 (2004).CrossRefGoogle Scholar
52Felix, N., Ober, C.K., Chem. Mater. 20, 2932 (2008).CrossRefGoogle Scholar
53Felix, N.M., Tsuchiya, K., Ober, C.K., Adv. Mater. 18, 442 (2006).CrossRefGoogle Scholar
54Yoshiwa, M., Kageyama, H., Shirota, Y., Wakaya, F., Gamo, K., Takai, M., Appl. Phys. Lett. 69, 2605 (1996).CrossRefGoogle Scholar
55Chang, S.W., Ayothi, R., Bratton, D., Yang, D., Felix, N., Cao, H.B., Deng, H., Ober, C.K., J. Mater. Chem. 16, 1470 (2006).CrossRefGoogle Scholar
56Malliaras, G., Friend, R., Phys. Today 58, 53 (2005).CrossRefGoogle Scholar
57Hwang, H.S., Zakhidov, A.A., Lee, J.-K., Andre, X., DeFranco, J.A., Fong, H.-H., Holmes, A.B., Malliaras, G.G., Ober, C.K., J. Mater. Chem. 18, 3087 (2008).CrossRefGoogle Scholar
58Luscombe, C.K., Huck, W.T.S., Holmes, A.B., Lu, T., Leeke, G.A., Santos, R.C.D., Al-Duri, B., Seville, J.P.K., Mater. Res. Soc. Symp. Proc. 734, 103 (2003).Google Scholar
59Li, L., Counts, K.E., Kurosawa, S., Teja, A.S., Collard, D.M., Adv. Mater. 16, 180 (2004).CrossRefGoogle Scholar
60Luscombe, C.K., Proemmel, S., Huck, W.T.S., Holmes, A.B., Fukushima, H., J. Org. Chem. 72, 5505 (2007).CrossRefGoogle Scholar