Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2011

Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface

Résumé

The synthesis and characterization of a series of quaterthiophenes (4Ts) with thiolate groups protected with 2-cyanoethyl (CNE), 2-trimethylsilylethyl (TMSE), and acetyl (Ac) groups are described. Sequential cleavage of these different protecting groups allows for the preparation of 4Ts derivatized with ferrocene and/or alkanethiol chains. The electrochemical behavior of these compounds has been analyzed in solution by cyclic voltammetry (CV). A ferrocene-derivatized dithiol 4T 14 and a dithiol 4T 15 with two TMSE-protected thiolate groups have been immobilized on a gold surface as monolayers that have been characterized by CV, ellipsometry, contact-angle measurement, and X-ray photoelectron spectroscopy (XPS). The results show that molecules 14 and 15 are doubly grafted with a horizontal orientation of the conjugated system relative to the surface. Furthermore, application of the deprotection/alkylation sequence of the remaining protected thiolate groups on a monolayer of 15 allows for efficient post-functionalization.

Domaines

Matériaux

Dates et versions

hal-01122036 , version 1 (03-03-2015)

Identifiants

Citer

Truong Khoa Tran, Quentin Bricaud, Maitena Ocafrain, Philippe Blanchard, Jean Roncali, et al.. Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface. Chemistry - A European Journal, 2011, 17, pp.5628 - 5640. ⟨10.1002/chem.201003687⟩. ⟨hal-01122036⟩
282 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More