High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins.
In noncoordinating solvents, meso-cinchomeronimide appended Zn(II) porphyrin 2 forms a cyclic trimer, while diporphyrins 7 exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants from 7(in-in), 7(in)(-)(out), and 7(out-out), respectively, through almost perfect discrimination of enantiomeric and conformational differences of the meso-cinchomeronimide substituents. In the latter self-sorting processes, the dihedral angles dictated by the two pyridyl nitrogen atoms control the size of the aggregates; the trimer from 7(in-in), the tetarmer from 7(in)(-)(out), and the pentamer from 7(out-out). Cyclic structures of (2)(3) and (R-7(out-out))(5) have been determined by single-crystal X-ray diffraction analysis.
Kamada
Taisuke
T
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan.
Aratani
Naoki
N
Ikeda
Toshiaki
T
Shibata
Naoki
N
Higuchi
Yoshiki
Y
Wakamiya
Atsushi
A
Yamaguchi
Shigehiro
S
Kim
Kil Suk
KS
Yoon
Zin Seok
ZS
Kim
Dongho
D
Osuka
Atsuhiro
A
D040761:Biomimetic Materials / Q000737:chemistry*; D002942:Circular Dichroism; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008665:Metalloporphyrins / Q000737:chemistry*; D008968:Molecular Conformation; D009539:Nicotinic Acids / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D007094:Imides; D008665:Metalloporphyrins; D009539:Nicotinic Acids; D011725:Pyridines; C522553:meso-cinchomeronimide; D009584:Nitrogen