Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 9619-9630Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00790
Keywords
-
Categories
Funding
- National Science Foundation [CHE-1058846]
- NSF Fellowship [HRD-1400382]
- Departments of Chemistry at Fudan University
- University of Connecticut
- National Science Foundation of the United States through the Major Research Instrumentation Program [CHE-1625543]
Ask authors/readers for more resources
A novel and efficient synthetic pathway toward known meso-tetraphenylporpholactams, also applicable to the synthesis of hitherto unknown and inaccessible meso-C6F5-substituted porpholactam, is detailed (dioxochlorin -> dioxochlorin urea adduct -> porpholactam). meso-Tetraphenylporpholactam was converted to an imidazoloporphyrin-alpha-triflate derivative that was demonstrated to be of utility for the generation of functionalized imidazoloporphyrins with a substituted amine adjacent to the outside N atom of the imidazole moiety (using pyridine, Et2NH, diethyliminodiacetic acetate, dipicolylamine (DPA), and cyclen). The DPA- and iminodiacetate-imidazoloporphyrin conjugates were structurally characterized. The chemosensing potential of the metal chelate-imidazoloporphyrin conjugates was evaluated, though their constrained metric parameters led to muted chemosensing responses to various divalent metal ions. The accessibility of the meso-arylporpholactams and the meso-tetraphenylimidazoloporphyrin triflate enables the continued exploration of porphyrin-like pyrrole-modified porphyrins that incorporate a nitrogen atom in place of a beta-carbon atom in their macrocycles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available