TY - JOUR
T1 - An electron-deficient porphyrin tape
AU - Mori, Hirotaka
AU - Tanaka, Takayuki
AU - Aratani, Naoki
AU - Lee, Byung Sun
AU - Kim, Pyosang
AU - Kim, Dongho
AU - Osuka, Atsuhiro
PY - 2012/8
Y1 - 2012/8
N2 - Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) 3. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S 1-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.
AB - Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf) 3. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S 1-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.
UR - http://www.scopus.com/inward/record.url?scp=84863856480&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84863856480&partnerID=8YFLogxK
U2 - 10.1002/asia.201200247
DO - 10.1002/asia.201200247
M3 - Article
C2 - 22615269
AN - SCOPUS:84863856480
SN - 1861-4728
VL - 7
SP - 1811
EP - 1816
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 8
ER -