The adsorption of uracil on Au(100) has been studied by in-situ scanni
ng tunneling microscopy (STM). Defending on the potential applied to t
he gold electrode? uracil forms three highly ordered monolayers, which
were imaged with molecular resolution. ''Steady state'' and time-depe
ndent experiments were performed to follow structural changes of the r
espective substrate surface in the presence of these organic layers. A
physisorbed film of planar oriented and via hydrogen bonds connected
molecules exists at negative electrode charges. Coupled with changes o
f the electronic state of adsorbed uracil this monolayer undergoes a f
irst order phase transition when altering the electrode potential towa
rds more positive values. A third (chemisorbed) adlayer is finally for
med simultaneously with the substrate surface structural transition (h
ex) --> (1 x 1). Uracil changes its orientation from planar to perpend
icular, and a substrate specific surface coordination complex is creat
ed. The ''equilibrium structure'' is determined by the competing actio
n of substrate-adsorbate coordination and lateral stacking interaction
s. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.