Abstract
The synthesis of five light absorbing triazolobithiophenic thiols, which were utilized for producing self-assembled monolayers (SAMs) on gold surfaces, is presented. The monolayer formation was monitored by cyclic voltammetry, indicating excellent surface coverage. The new triazolobithiophenic compounds exhibited an absorption maximum around 340 nm, which is close to the emission wavelength of a standard nitrogen laser. Consequently these compounds could be used to aid ionization in laser desorption mass spectrometry (MS).
Highlights
Light absorbing self-assembled monolayers (SAMs) offer very interesting properties for various scientific and technical applications [1,2,3,4,5,6]
Earlier experiments have shown that the S-acetylated derivative of 1 [Figure 1a] exhibits an absorption maximum of 340 nm, which is close to the emission wavelength of a standard nitrogen laser (337 nm) [3]
Alkynylbithiophenes 6a–c and azidoalkylbithiophenes 7a,b were synthesized from 3-(5'-(methylthio)-2,2'-bithiophen-5-ylthio)propanenitrile following a strategy proposed by Becher et al [3,43] and underwent a copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition under classical Sharpless conditions, yielding respectively high amounts of triazole linked bithiophenes 4a–c and 5a,b (Scheme 1) [44]
Summary
Light absorbing self-assembled monolayers (SAMs) offer very interesting properties for various scientific and technical applications [1,2,3,4,5,6]. With respect to the DIAMS application these properties were preserved in all the new molecules Apart from these selective features, surface coverage together with long term stability represent crucial parameters for the quality of SAMs. The most basic bithiophenic SAM was produced by attaching a bithiophene moiety to a –(CH2)n–SH side chain of desired length, as previously described [3]. As changing the methyl group at the surface of SAMs requires a synthetic strategy with a complex desymmetrisation of the initial bithiophene, the authors decided to explore the effect of an extra aromatic ring in the subterminal part of the monolayer In this context, the introduction of a 1,2,3-triazole ring appeared to be a good starting point, because the synthesis of the corresponding triazolobithiophene derivative could be achieved by a convergent click reaction.
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