Preparation of Polyetherol-Appended Sulfur Porphyrazines and Investigations of Peripheral Metal Ion Binding in Polar Solvents

• Published in: Inorganic chemistry Vol. 39; no. 18; pp. 3963 - 3969
• Main Authors: Ehrlich, Lori A, Skrdla, Peter J, Jarrell, Wade K, Sibert, John W, Armstrong, Neal R, Saavedra, S. Scott, Barrett, Anthony G. M, Hoffman, Brian M
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 04.09.2000
• Subjects: Ethers - chemical synthesis; Metals - chemistry; Molecular Structure; Porphyrins - chemical synthesis; Solvents; Spectrum Analysis; Sulfur - chemistry
• ISSN: 0020-1669; 1520-510X
• DOI: 10.1021/ic991033m

We describe the complete synthesis and characterization of a new family of peripherally functionalized porphyrazines (pz's) with four, three, or two (in a trans conformation) bis[thioethoxy(ethoxy)ethanol] moieties appended at the pyrroles. These “polyetherol” groups serve as weak exocyclic binding sites for a number of metal ions and also provide solubility of the pz's in low molecular-weight alcohols and water. Electronic spectra of the modified porphyrazines exhibit distinct changes in the visible region (both absorbance and fluorescence) in response to treatment with Ag+, Pb2+, Cd2+, Cs+, and Ni2+ in solution. Such properties make these compounds intriguing candidates for incorporation into the transducer layers in optically based chemical sensors.