Application: SAM preparation, amine group coating

Chemical Description: 11-Hydroxyundecylphosphonic acid
CAS: 83905-98-0

Appearance: White to slightly yellow powder
MW: C11H25O4P, 252.29

Storage Condition: ambient temperature
Shipping Condition: ambient temperature


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Structural Formula

Product Description
Phosphonic acid derivatives are used for surface modification on oxidized metals such as Al2O31), TiO22), ZrO23), SiO24), Mica5), stainless(SS316L) 6), nitinol7), hydroxyapatite8), AgO9), ZnO10), ITO11,12).
For a long time, organosilanes have been used to form self assembled monolayer (SAM) on the metal oxide. However, it is not always adaptable in the applications due to the poor stability and polymerization of the reagent with each other. On the other hand, phosphonic acid derivatives equally form a SAM on the metal oxide despite being very stable compounds. Also, phosphonic acid derivatives have been reported to use formation of more stable and dense SAM than organosilanes. Klauk et. al. and Sekitani et. al. show alkyl phosphonate SAM on Al2O3 is more useful than the trichlorosilane derivatives SAM as an conductor film of an organic transistor13).
11-HUPA is an alkyl phosphonic acid derivative containing hydroxyl termination. Pulsipher et. al. prepare two different patterns of surfaces (aldehyde and carboxylic acid) by controlling oxidizing condition on the ITO substrate modified with 11-HUPA12).

When it is difficult to take out all the powder from the container,
please add the solvent into a container and dissolve it before its use.

1) T. Hauffman, O. Blajiev, J. Snauwaert, C. van Haesendonck, A. Hubin, H. Terryn,  EStudy of the self-assembling of n-octylphosphonic acid layers on aluminum oxide E Langmuir, 2008, 24 (23), 13450.
2) B. M. Silverman, K. A. Wieghaus, J. Schwartz, “Comparative properties of siloxane vs phosphonate monolayers on a key titanium alloy E Langmuir, 2005, 21(1), 225.
3) W. Gao, L. Reven, “Solid-state NMR-studies of self-assembled monolayers E Langmuir 1995, 11 (6), 1860.
4) E. L. Hanson, J. Schwartz, B. Nickel, N. Koch, M. F. Danisman, “Bonding self-assembled, compact organophosphonate monolayers to the native oxide surface of silicon E J. Am. Chem. Soc. 2003, 125 (51), 16074.
5) J. T. Woodward, A. Ulman, D. K. Schwartz, “Self-assembled monolayer growth of octadecylphosphonic acid on mica E Langmuir 1996, 12 (15), 3626.
6) A. Raman, M. Dubey, I. Gouzman and E. S. Gawalt, “Formation of self-assembled monolayers of alkylphosphonic acid on the netive oxide surface of SS316L E Langmuir, 2006, 22, 6469.
7)  R. Quinones and E. S. Gawalt, “Polystyrene formation on monolayer-modified nitinol effectively controls corrosion E Langmuir, 2008, 24, 10858.
8) S. C. D’Andrea and Al. Y. Fadeev, “Covalent surface modification of calcium hydroxyapatite using n-alkyl- and n-fluoroalkylphosphonic acids EB>, Langmuir, 2003, 19, 7904.
9) Y. T. Tao, C. Y. Huang, D. R. Chiou, L. J. Chens, “Infrared and atomic force microscopy imaging study of the reorganization of self-assembled monolayers of carboxylic acids on silver surface E Langmuir, 2002, 18, 8400.
10) B. Zhang, T. Kong, W. Xu, R. Su, Y. Gao and G. Cheng, “Surface functionalization of zinc oxide by carboxyalkylphosphonic acid self-assembled monolayers E Langmuir, 2010, 26(6), 4514.
11) A. Sharma, B. Kippelen, P. J. Hotchkiss and S. R. Marder, “Stabilization of the work function of indium tin oxide using organic surface modifiers in organic light-emitting diodes E Appl. Phys. Lett., 2008, 93, 163308.
12) A. Pulsipher, N. P. Westcott, W. Luo, and M. N. Yousaf, “Rapid in situ generation of two patterned chemoselective surface chemistries from a single hydroxy-terminated surface using controlled microfluidic oxidation E J. Am. Chem. Soc., 2009, 131(22), 7626
13) a) H. Klauk, U. Zschieschang, J. Pflaum, M. Halik,  E/SPAN>Ultralow-power organic complementary circuits E Nature, 2007, 445, 745. b) T. Sekitani, Y. Noguchi, U. Zschieschang, H. Klauk, T. Someya, “Organic transistors manufactured using inkjet technology with subfemtoliter accuracy E Proc. Natl. Acad. Sci. USA, 2008, 105, 4976

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Surface Chemistry

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