Syntheses and characterizations of a new calixarene-porphyrin conjugate as electron transfer system.
A new calixarene-based donor-acceptor system, cone conformer 1, was prepared for the first time. In this compound, the calix[4]arene serves to juxtapose a tri-chloroquinone acceptor near the porphyrin photo-donor plane. As to the conformational control, the cone conformer 1 gave two peaks of phenolic OH groups at 8.40 and 8.43 ppm. This shows that cone conformer 1 is stabilized by intramolecular hydrogen bonds. The fluorescence intensity of 1 was 35% of that for the control compound 2. This means the tri-chloroquinone group in 1 efficiently quenched the fluorescence of ZnP*. The shortest edge-to-edge separation of the chromophores of 1 is ca. 8 A (as judged by CPK models). This provides a new calixarene-based supramolecular system in which through-space donor-to-acceptor electron transfer is observed upon photoexcitation.
Arimura
Takashi
T
Nanotechnology Research Institute, AIST, Tsukuba, Japan. takashi-arimura@aist.go.jp
Ide
Seiji
S
Suga
Yasuhiro
Y
Tachiya
Masanori
M
D047250:Calixarenes / Q000737:chemistry*; D004583:Electrons; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry; D013050:Spectrometry, Fluorescence
D011166:Porphyrins; D011809:Quinones; D047250:Calixarenes