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Creating Favorable Geometries for Directing Organic Photoreactions in Alkanethiolate Monolayers

Science  11 Mar 2011:
Vol. 331, Issue 6022, pp. 1312-1315
DOI: 10.1126/science.1200830

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  1. Fig. 1

    Structures of 2-anthracenethiol and 10-thiodecyl 2-anthryl ether are compared to structures of 9-(4-mercaptophenylethynyl)anthracene (MPEA, 1), 9-phenylethynylanthracene disulfide (2), and oligo(phenylene-ethynylene)thiol (OPE, 3).

  2. Fig. 2

    Schematic view of the photoreaction of 9-phenylethynylanthracene (PEA) in solution (26).

  3. Fig. 3

    Schematic view of the photoreaction of 9-(4-mercaptophenylethynyl)anthracene on a Au{111} surface.

  4. Fig. 4

    A to C) Sequential STM images of inserted MPEA molecules in a C12 SAM matrix. Yellow and red boxes show the apparent height changes of molecules. (D to I) Cropped sequential STM images of molecular switching. The arrows at the bottom of images (A) to (C) highlight molecules that show no substantial conductance changes during imaging. Imaging conditions were sample bias voltage (Vsample) = –1.0 V and tunneling current (Itunnel) = 1.0 pA.

  5. Fig. 5

    A to C) STM images of MPEA molecules inserted into a C12 SAM matrix and then exposed to UV light (~365 nm). Images were collected during irradiation after 24 min (A), 124 min (B), and 220 min (C). Imaging conditions were Vsample = –1.0 V and Itunnel = 1.0 pA. The UV illumination increases the apparent height of photoreactive molecules, and more molecules appear as protrusions at longer irradiation (arrows). Several pairs of molecules show substantial decreases in apparent height, attributed to photodimerization [boxes in (B) and (C)].