A series of rigid and conformationally restricted cyclic bis(zinc porphyrin)s connected via 2,2'-bipyridine and phthalamide, isophthalamide, or terephthalamide moieties were prepared by metal-templated synthesis. The yields were significantly improved when compared with those obtained under metal-free conditions. In particular, phthalamide and terephthalamide derivatives were obtained only by metal-templated synthesis. Structural analyses and dynamics of the exchange between the conformers in each cyclic porphyrin were examined by NMR spectroscopy. Although the distances between the two zinc porphyrins were extended in the order of phthalamide, isophthalamide, and terephthalamide derivatives, the order of the specific retention of the cyclic porphyrins on cyanopropyl-modified silica gel (CN-MS) chromatography columns varied. Thus, this order was reversed in the isophthalamide and terephthalamide derivatives. Based on the rigid structure of the terephthalamide derivative, the origin of the specific retention on the CN-MS chromatography column was attributed to both the distance and rigidity of the cyclic porphyrins.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d1ob00088hDOI Listing

Publication Analysis

Top Keywords

metal-templated synthesis
12
specific retention
12
isophthalamide terephthalamide
12
terephthalamide derivatives
12
rigid conformationally
8
conformationally restricted
8
restricted cyclic
8
cyanopropyl-modified silica
8
silica gel
8
phthalamide isophthalamide
8

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!