scholarly journals Reflection Absorption Infrared Spectroscopy Characterization of SAM Formation from 8-Mercapto-N-(phenethyl)octanamide Thiols with Phe Ring and Amide Groups

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5633
Author(s):  
Zenonas Kuodis ◽  
Ieva Matulaitienė ◽  
Marija Špandyreva ◽  
Linas Labanauskas ◽  
Sigitas Stončius ◽  
...  

Multifunctional amide-containing self-assembled monolayers (SAMs) provide prospects for the construction of interfaces with required physicochemical properties and distinctive stability. In this study, we report the synthesis of amide-containing thiols with terminal phenylalanine (Phe) ring functionality (HS(CH2)7CONH(CH2)2C6H5) and the characterization of the formation of SAMs from these thiols on gold by reflection absorption infrared spectroscopy (RAIRS). For reliable assignments of vibrational bands, ring deuterated analogs were synthesized and studied as well. Adsorption time induced changes in Amide-II band frequency and relative intensity of Amide-II/Amide-I bands revealed two-state sigmoidal form dependence with a transition inflection points at 2.2 ± 0.5 and 4.7 ± 0.5 min, respectively. The transition from initial (disordered) to final (hydrogen-bonded, ordered) structure resulted in increased Amide-II frequency from 1548 to 1557 cm−1, which is diagnostic for a strongly hydrogen-bonded amide network in trans conformation. However, the lateral interactions between the alkyl chains were found to be somewhat reduced when compared with well-ordered alkane thiol monolayers.

2009 ◽  
Vol 25 (1) ◽  
pp. 83-86 ◽  
Author(s):  
Guo-Qiang TAN ◽  
Hai-Yang BO ◽  
Hong-Yan MIAO ◽  
Ao XIA ◽  
Zhong-Liang HE

Langmuir ◽  
2017 ◽  
Vol 33 (25) ◽  
pp. 6419-6426 ◽  
Author(s):  
A. Shaheen ◽  
J. M. Sturm ◽  
R. Ricciardi ◽  
J. Huskens ◽  
C. J. Lee ◽  
...  

1999 ◽  
Vol 77 (5-6) ◽  
pp. 1077-1084 ◽  
Author(s):  
R Scott Reese ◽  
Marye Anne Fox

Self-assembled monolayers of sulfur-terminated oligonucleotide duplexes were formed on flat gold surfaces, either by exposure of a self-assembled monolayer bearing one oligonucleotide strand to the complementary strand or by preformation of a oligonucleotide duplex that was then deposited on a fresh gold surface. Virtually identical spectral behavior was observed whether the duplex was produced before deposition or by in situ complementary association. With a duplex bearing an appropriate pyrene end-label, the resulting thin film was photoresponsive. Surface emission measurements show no evidence for pyrene aggregation on the modified surfaces. The polarity of the photocurrent, reflecting photoinduced electron transfer initiated by photoexcitation of pyrene, is opposite that expected from the oligonucleotide-mediated reduction of the appended pyrene excited state.Key words: oligonucleotide, self-assembled monolayer, duplex formation, photoelectrochemistry, surface emission.


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