Preparation of polyetherol-appended sulfur porphyrazines and investigations of peripheral metal ion binding in polar solvents.
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.
Ehrlich
L A
LA
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Skrdla
P J
PJ
Jarrell
W K
WK
Sibert
J W
JW
Armstrong
N R
NR
Saavedra
S S
SS
Barrett
A G
AG
Hoffman
B M
BM
D004987:Ethers / Q000138:chemical synthesis*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis*; D012997:Solvents; D013057:Spectrum Analysis; D013455:Sulfur / Q000737:chemistry*
D004987:Ethers; D008670:Metals; D011166:Porphyrins; D012997:Solvents; D013455:Sulfur