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Electroactive self-assembled monolayers of unique geometric structures by using rigid norbornylogous bridges

Darwish, N ; Eggers, PK ; Da Silva, PA ; Zhang, Y ; Tong, Y ; Ye, S ; Gooding, Jj ; Paddon-Row, Mn

ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201101588

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  • Nhan đề:
    Electroactive self-assembled monolayers of unique geometric structures by using rigid norbornylogous bridges
  • Tác giả: Darwish, N ; Eggers, PK ; Da Silva, PA ; Zhang, Y ; Tong, Y ; Ye, S ; Gooding, Jj ; Paddon-Row, Mn
  • Chủ đề: Self-Assembled Monolayers ; Anthraquinone ; Electron Transfer ; in-Situ IR ; 03 Chemical Sciences ; Chemistry
  • Mô tả: Herein, we describe the synthesis of straight (S) and L‐shaped (L) norbornylogous bridges (NBs) with an anthraquinone moiety at the distal end as the redox‐active head group and two thiol feet at the proximal end, by which the molecules assemble on gold surfaces. The NB molecules were shown to form self‐assembled monolayers (SAMs) with a well‐behaved surface redox process. The SAMs were characterized by using in situ IR spectroscopy, cyclic voltammetry, scanning tunnelling microscopy and electrochemical impedance spectroscopy. The surface selection rules associated with the IR band intensities allowed the estimation of the position of the anthraquinone moiety with respect to the surface and the tilt of the bridge with respect to the surface normal, both in pure and diluted monolayers. It is shown that the S‐ and L‐NBs hold the plane of the anthraquinone moiety close to the surface normal or the surface tangent, respectively. Neither NB molecule changes its orientation if spaced by diluents on the surface. The difference in the structure of the S‐ and L‐NB SAMs provides a suitable framework for the investigation of factors that govern electron transfer of anthraquinone moieties across self‐assembled monolayers with limited structural ambiguity, as compared with the commonly used structurally flexible alkanethiol monolayers. : Rigid anthraquinone‐terminated norbornylogous bridges (NBs) have been synthesized and used to form monolayers in which the redox moiety has a well‐defined distance and orientation from the electrode surface. Each NB molecule attaches to the electrode surface through two CHSH groups in a relationship. Straight (S) and L‐shaped (L) NBs place the anthraquinone moiety close to the surface normal and tangent, respectively (see figure).
  • Ngôn ngữ: English
  • Số nhận dạng: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201101588

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