TY - JOUR
T1 - Chiral self-discriminative self-assembling of meso-meso linked diporphyrins
AU - Maeda, Chihiro
AU - Kamada, Taisuke
AU - Aratani, Naoki
AU - Osuka, Atsuhiro
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research on Priority Area (No. 18033028, Coordination Space) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
PY - 2007/11
Y1 - 2007/11
N2 - We have explored a variety of self-assembled cyclic porphyrin arrays mainly as biomimetic models of light harvesting antenna in photosynthetic systems. The key reaction is Ag(I)-promoted coupling reaction of 5,15-diaryl zinc(II) porphyrin that provides a meso-meso linked diporphyrin. meso-Pyridine-appended zinc(II) porphyrins M1-M3 and their meso-meso linked dimers D1-D3 assemble spontaneously in non-coordinating solvents into tetrameric porphyrin squares S1-S3 and porphyrin boxes B1-B3, respectively. In the latter case, it has been demonstrated that four molecules of R-diporphyrin assemble into R-box and four molecules of S-diporphyrin assemble into S-box via rigorous homochiral self-sorting process. Efficient excitation energy transfer along these cyclic porphyrin arrays has been revealed by the time-resolved transient absorption and fluorescence measurements. We have also demonstrated that the meso-cinchomeronimide appended Zn(II) porphyrin CIM forms a cyclic trimer, while the corresponding diporphyrins CID exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants, through perfect discrimination of enantiomeric and conformational differences of the meso-cinchomeronimide substituents.
AB - We have explored a variety of self-assembled cyclic porphyrin arrays mainly as biomimetic models of light harvesting antenna in photosynthetic systems. The key reaction is Ag(I)-promoted coupling reaction of 5,15-diaryl zinc(II) porphyrin that provides a meso-meso linked diporphyrin. meso-Pyridine-appended zinc(II) porphyrins M1-M3 and their meso-meso linked dimers D1-D3 assemble spontaneously in non-coordinating solvents into tetrameric porphyrin squares S1-S3 and porphyrin boxes B1-B3, respectively. In the latter case, it has been demonstrated that four molecules of R-diporphyrin assemble into R-box and four molecules of S-diporphyrin assemble into S-box via rigorous homochiral self-sorting process. Efficient excitation energy transfer along these cyclic porphyrin arrays has been revealed by the time-resolved transient absorption and fluorescence measurements. We have also demonstrated that the meso-cinchomeronimide appended Zn(II) porphyrin CIM forms a cyclic trimer, while the corresponding diporphyrins CID exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants, through perfect discrimination of enantiomeric and conformational differences of the meso-cinchomeronimide substituents.
KW - Chiral recognition
KW - Porphyrin
KW - Self-assembly
KW - Self-sorting
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U2 - 10.1016/j.ccr.2007.02.017
DO - 10.1016/j.ccr.2007.02.017
M3 - Review article
AN - SCOPUS:35248831587
VL - 251
SP - 2743
EP - 2752
JO - Coordination Chemistry Reviews
JF - Coordination Chemistry Reviews
SN - 0010-8545
IS - 21-24
ER -