Synthesis and properties of Oxasmaragdyrins containing one Five-membered Heterocycle at Meso-position
نویسندگان
چکیده
The oxasmaragdyrins containing one five membered heterocycle such as pyrrole, thiophene and furan in place of one of the meso-phenyl group were synthesized by acid-catalyzed oxidative coupling reaction of meso-heterocycle substituted dipyrromethane with 16-oxatripyrrane in the presence of catalytic amount of trifluoroacetic acid followed by oxidation with DDQ. The smaragdyrin macrocycles containing one fivemembered heterocycle at meso-position were characterized by HR-MS and detailed 1D and 2D NMR studies. The absorption and fluorescence studies revealed that the presence of five membered heterocycle at mesoposition of smaragdyrin resulted in bathochromic shifts in absorption and emission bands with slight reduction in quantum yields compared to smraragdyrin macrocycle containing six membered meso-phenyl groups. The electrochemical studies revealed that the meso-heterocycle smaragdyrins are electron deficient compared to meso-phenyl smaragdyrins.
منابع مشابه
Synthesis and antimicrobial activity of cephalosporins with a 1-pyridinium substituent carrying a 5-membered heterocycle at the C-3 position.
A series of potent antimicrobial agents have been prepared. These derivatives are cephalosporins carrying a pyridine ring substituted with a heterocycle in the C-3 position. Some of them showed excellent activity not only against Gram-negative organisms including Pseudomonas aeruginosa but also against Gram-positive ones. In view of their biological and physico-chemical properties, 7 beta-[2-(2...
متن کاملPredicting Young’s Modulus of Aggregated Carbon Nanotube Reinforced Polymer
Prediction of mechanical properties of carbon nanotube-based composite is one of the important issues which should be addressed reasonably. A proper modeling approach is a multi-scale technique starting from nano scale and lasting to macro scale passing in-between scales of micro and meso. The main goal of this research is to develop a multi-scale modeling approach to extract mechanical propert...
متن کاملA Survey of Anticancer Effect of Some Five- and Six-Membered Palladium (II) Complexes (Containing Bidentate Phosphorus Ligands) on Caco-2 Colon Cancer Cell Line
Background and Objectives: Transition metal complexes possess a variety of biological and pharmacological activities, such as antitumor, antimicrobial, anti-inflammatory, anti-diabetic, and free radical scavenging. Many studies have been carried out on platinum-based chemotherapy agents, however, most attention has been paid to non-platinum metal-based agents in order to find different metal comp...
متن کاملUnique prototropy of meso-alkylidenyl carbaporphyrinoid possessing one meso-exocyclic double bond.
Generic synthesis, identification of structural identity, unique prototropy and spectroscopic properties of meso-alkylidenyl-thia(m-benzi)porphyrinoid containing one exocyclic double bond at the meso-position were presented.
متن کاملArylazoindazole Photoswitches: Facile Synthesis and Functionalization via SNAr Substitution
A straightforward synthetic route to arylazoindazoles via nucleophilic aromatic substitution is presented. Upon deprotonation of the NH group, a C6F5-substituted formazan undergoes facile cyclization as a result of intermolecular nucleophilic substitution (SNAr). This new class of azo photoswitches containing an indazole five-membered heterocycle shows photochemical isomerization with high fati...
متن کامل