Thioacetyl-terminated ferrocene-anthraquinone conjugates: synthesis, photo- and electrochemical properties triggered by protonation-induced intramolecular electron transfer.
Two thioacetyl-terminated ferrocene-anthraquinone donor-acceptor molecules with different pi-electron conjugative units have been synthesized via a series of Stille and Sonagashira reactions. Their photochemical and electrochemical properties before and after addition of an organic acid are investigated, indicating that these complexes are sensitive to external perturbation of protonation, leading the structural change to an expansion of pi-conjugated system by cyclocondensation reaction and promoting intramolecular electron transfer from donor to acceptor. They would be good candidates for studies of novel SAMs, and the properties triggered by protonation-induced intramolecular electron transfer will make the SAMs be useful in designing new functional molecular devices.
Zhang
Wen-Wei
WW
Department of Chemistry, School of Science, the University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kondo
Mio
M
Fujita
Takako
T
Namiki
Kosuke
K
Murata
Masaki
M
Nishihara
Hiroshi
H
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D055664:Electrochemical Techniques; D004563:Electrochemistry; D004566:Electrodes; D004583:Electrons; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D000075163:Metallocenes; D055668:Photochemical Processes; D011522:Protons; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000880:Anthraquinones; D005296:Ferrous Compounds; D000075163:Metallocenes; D011522:Protons; D013438:Sulfhydryl Compounds; D006046:Gold; C004998:ferrocene