New cruciform structures: toward coordination induced single molecule switches.
New cruciform structures 1-4 were synthesized to investigate a new single molecule switching mechanism arising from the interplay between the molecule and the electrode surface. These molecular cruxes consist of two rod-type substructures, namely an oligophenylenevinylene and an oligophenyleneethynyl. While the oligophenylenevinylene rods are functionalized with acetyl protected sulfur anchor groups, the oligophenyleneethynyl rods provide terminal pyridine units. The hypothesized switching mechanism should arise from the electrochemical potential dependent coordination of the pyridine unit to the electrode surface. The assembly of the oligophenylenevinylene substructure was based on a Wittig reaction whereas its perpendicular oligophenyleneethynyl rod was assembled by Sonogashira-Hagihara coupling reactions. Preliminary transport investigations with molecular cruciforms 2 and 4 in a mechanical controllable break junction in a liquid environment displayed the trapping of single molecules between two gold electrodes via the terminally sulfur functionalized oligophenylenevinylene rod.
Grunder
Sergio
S
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
Huber
Roman
R
Horhoiu
Viviana
V
González
Maria Teresa
MT
Schönenberger
Christian
C
Calame
Michel
M
Mayor
Marcel
M
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D004566:Electrodes; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D011145:Polyvinyls / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013499:Surface Properties
D000480:Alkynes; D004987:Ethers; D011145:Polyvinyls; D013438:Sulfhydryl Compounds; C436384:phenyleneethynylene; C470024:poly(4-phenylenevinylene); D006046:Gold