A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety

Physical Chemistry Chemical Physics : PCCP
Somsakul WatcharinyanonL S O Johansson

Abstract

Porphyrin-functionalized oligo(phenyleneethynylene)s (OPE) are promising molecules for molecular electronics applications. Three such molecules (1-3) with the common structure P-OPE-AG (P and AG are a porphyrin and anchor group, respectively) and different anchor groups, viz. an acetyl protected thiol, -S-COCH3 (1), an acetyl protected thiol with methylene linker, -CH2-S-COCH3 (2), and a trimethylsilylethynyl group, -C(triple bond)C-Si(CH3)3 (3) have been synthesized and the corresponding self-assembled monolayers (SAMs) on Au(111) substrates have been prepared. The integrity and structural properties of these films were studied by X-ray photoelectron spectroscopy and near-edge X-ray absorption fine structure spectroscopy. The results suggest that the films formed from 1 have a high orientational order with an almost upright orientation and dense packing of the molecular constituents, i.e. represent a high quality SAM. In contrast, molecule 2 formed disordered molecular layers on Au, even though the molecule-surface bonding (thiolate) is the same as in the case of molecule 1. This suggests that the methylene linker in molecule 2 has a strong impact on the quality of the resulting film, so that a well-ordered SAM cannot be forme...Continue Reading

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Citations

Jun 7, 2015·Annual Review of Analytical Chemistry·Richard J Nichols, Simon J Higgins
Aug 27, 2016·Journal of the American Chemical Society·Nathaniel T KimJames L Leighton
Oct 30, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Santiago Marqués-GonzálezPaul J Low
Aug 31, 2018·The Journal of Physical Chemistry Letters·I Lucia HerrerPilar Cea

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