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Thiophoshonates



Alkylphosphonic and alkylphosphoric acids are less often characterized compared to silanes and thiols, but they are the becoming of great practical interest because of their ability to produce SAMs on a range of metal oxide surfaces (TiO2 [1], ZrO2 [2], Al2O3 [2], Ta2O5 [2], Nb2O5 [2], ITO[3], MgO[4] ect.). The reaction of long-chain alkylphosphonic [5] or phosphoric [6] acids with metal oxide supports leads to dense, well-ordered SAMs. Phosphonates and phosphonic acids form SAMs on metal surfaces by the formation of metal-O-P bonds. The deposition technique is based on SAMs made from aqueous alkyl phosphate solutions, which has the advantage of not using organic solvents [2]. However, well-ordered SAMs can be also obtained from organic solutions as well. Advantages of these SAMs compared to silane ones are a higher hydrolytic stability under physiological conditions and the fact that no surface conditioning (i.e., acid treatment) is required to obtain high coverage[7]. We have developed the a range of alkylthiophosphates bearing additional functional groups (OH, EG3OH, NH2, COOH, CONHS) at terminal position, what allows further elaboration of SAMs by chemical attachment of relevant molecules.

[1] M. Gnauck, E. Jaehne, T. Blaettler, S. Tosatti, M. Textor, H. J. P. Adler, Carboxy-Terminated Oligo(ethylene glycol)-Alkane Phosphate: Synthesis and Self-Assembly on Titanium Oxide Surfaces, Langmuir, 2007, 23, 377-381.

[2] R. Hofer, M. Textor and N. D. Spencer, Alkyl Phosphate Monolayers Self-Assembled from Aqueous Solution onto Metal Oxide Surfaces, Langmuir, 2001, 17, 4014-4020.

[3] A. Jedaa, M. Burkhardt, U. Zschieschang, H. Klauk, D. Habich, G. Schmid, M. Halik, The impact of self-assembled monolayer thickness in hybrid gate dielectrics for organic thin-film transistors, Org. Electron., 2009, 10, 1442-1447. [4] T. Ishizaki, M. Okido, Y. Masuda, N. Saito, M. Sakamoto, Corrosion Resistant Performances of Alkanoic and Phosphonic Acids Derived Self-Assembled Monolayers on Magnesium Alloy AZ31 by Vapor-Phase Method, Langmuir, 2011, 27, 6009-6017

[5] C. Queffelec, M. Petit, P. Janvier, D. A. Knight, B. Bujoli, Surface Modification Using Phosphonic Acids and Esters, Chem. Rev. , 2012, 112, 3777-3807.

[6] S. Tosatti, R. Michel, M. Textor and N. D. Spencer, Self-Assembled Monolayers of Dodecyl and Hydroxy-Dodecyl Phosphates on Both Smooth and Rough Titanium and Titanium Oxide Surfaces, Langmuir, 2002, 18, 3537-3548.

[7] B. M. Silverman, K. A. Wieghaus, and J. Schwartz, Comparative Properties of Siloxane vs Phosphonate Monolayers on A Key Titanium Alloy, Langmuir, 2005, 21, 225-228.



(HO)2-PO-S-(CH2)16-OHProduct structure:

Compound Cat. No. Weight
(HO)2-PO-S-C16-OH PO 001-0.1 100 mgPrice
PO 001-0.2 200 mgPrice
PO 001-0.5 500 mgPrice
PO 001-1 1 gPrice



(HO)2-PO-S-(CH2)m-COOHProduct structure:Detailed information:
Standard products:m: 10, 15

m Compound Cat. No. Weight
10 (HO)2-PO-S-C10-COOH PO 002-m10-0.1 100 mgPrice
PO 002-m10-0.2 200 mgPrice
PO 002-m10-0.5 500 mgPrice
PO 002-m10-1 1 gPrice
15 (HO)2-PO-S-C15-COOH PO 002-m15-0.1 100 mgPrice
PO 002-m15-0.2 200 mgPrice
PO 002-m15-0.5 500 mgPrice
PO 002-m15-1 1 gPrice



(HO)2-PO-S-(CH2)m-COONHSProduct structure:Detailed information:
Standard products:m: 10, 15

m Compound Cat. No. Weight
10 (HO)2-PO-S-C10-COONHS PO 003-m10-0.1 100 mgPrice
PO 003-m10-0.2 200 mgPrice
PO 003-m10-0.5 500 mgPrice
PO 003-m10-1 1 gPrice
15 (HO)2-PO-S-C15-COONHS PO 003-m15-0.1 100 mgPrice
PO 003-m15-0.2 200 mgPrice
PO 003-m15-0.5 500 mgPrice
PO 003-m15-1 1 gPrice



(HO)2-PO-S-(CH2)16-NH2Product structure:

Compound Cat. No. Weight
(HO)2-PO-S-C16-NH2 PO 004-0.1 100 mgPrice
PO 004-0.2 200 mgPrice
PO 004-0.5 500 mgPrice
PO 004-1 1 gPrice



(HO)2-PO-(CH2)17-MeProduct structure:

Compound Cat. No. Weight
(HO)2-PO-C17-Me PO 005-0.1 100 mgPrice
PO 005-0.2 200 mgPrice
PO 005-0.5 500 mgPrice
PO 005-1 1 gPrice



(HO)2-PO-S-(CH2)m-MeProduct structure:Detailed information:
Standard products:m: 15, 17

m Compound Cat. No. Weight
15 (HO)2-PO-S-C15-Me PO 006-m15-0.1 100 mgPrice
PO 006-m15-0.2 200 mgPrice
PO 006-m15-0.5 500 mgPrice
PO 006-m15-1 1 gPrice
17 (HO)2-PO-S-C17-Me PO 006-m17-0.1 100 mgPrice
PO 006-m17-0.2 200 mgPrice
PO 006-m17-0.5 500 mgPrice
PO 006-m17-1 1 gPrice



(HO)2-PO-S-(CH2)11-EGn-OHProduct structure:Detailed information:
Standard products:n: 3, 6

n Compound Cat. No. Weight
3 (HO)2-PO-S-C11-EG3-OH PO 007-n3-0.1 100 mgPrice
PO 007-n3-0.2 200 mgPrice
PO 007-n3-0.5 500 mgPrice
PO 007-n3-1 1 gPrice
6 (HO)2-PO-S-C11-EG6-OH PO 007-n6-0.1 100 mgPrice
PO 007-n6-0.2 200 mgPrice
PO 007-n6-0.5 500 mgPrice
PO 007-n6-1 1 gPrice



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