221108-22-1Relevant academic research and scientific papers
Novel core-modified expanded porphyrins with meso-Ary1 substituents: Synthesis, spectral and structural characterization
Narayanan, Seenichamy Jeyaprakash,Sridevi, Bashyam,Chandrashekar, Tavarekere K.,Vij, Ashwani,Roy, Raja
, p. 9053 - 9068 (1999)
The synthesis, spectral and structural characterization of meso-aryl sapphyrins and rubyrins containing heteroatoms such as S, O, Se in addition to pyrrole nitrogens are reported. The synthesis of the desired expanded porphyrins has been achieved using a
Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted- 21,23-ditellura/diselena core-modified porphyrinogens: Oxidation and detection of mercury(ii)
Ahmad, Sohail,Yadav, Kumar Karitkey,Singh, Sarangthem Joychandra,Chauhan
, p. 3171 - 3180 (2014/01/06)
Tellurium and selenium incorporated 5,10,15,20-meso-unsubstituted-21,23- ditellura/diselena core-modified porphyrinogens (N2Te2 and N2Se2), 5,10,15,20-meso-unsubstituted-21-tellura/selena core-modified porphyrinogens (N3Te and N3Se) and fully substituted meso-carbons porphyrinogens (N2Te2, N 2Se2 and higher analogs) are synthesized by 3 + 1 condensation of tellurophene/selenophene dipyrranes and their corresponding diols in the presence of BF3-etharate or BF3-methanol. The meso-unsubstituted and substituted porphyrinogens were oxidized with chloranil/0.1% aqueous FeCl3 in CHCl3 at room temperature to obtain the corresponding porphines and porphyrins which are further reduced to corresponding chlorin and bacteriochlorin, whereas the fully meso-substituted porphyrinogens were found to be good ligands for Hg2+. The structures of the products were characterized by IR, 1H, 13C, 125Te, 77Se NMR, CHN analysis, mass spectrometry and single-crystal XRD.
Water-soluble, core-modified porphyrins as novel, longer-wavelength-absorbing sensitizers for photodynamic therapy. II. Effects of core heteroatoms and meso-substituents on biological activity
Hilmey, David G.,Abe, Masako,Nelen, Marina I.,Stilts, Corey E.,Baker, Gary A.,Baker, Sheila N.,Bright, Frank V.,Davies, Sherry R.,Gollnick, Sandra O.,Oseroff, Allan R.,Gibson, Scott L.,Hilf, Russell,Detty, Michael R.
, p. 449 - 461 (2007/10/03)
Water-soluble, core-modified porphyrins were prepared and evaluated as sensitizers for photodynamic therapy (PDT). The addition of an aromatic aldehyde to 2,5-dilithiothiophene or -selenophene gave diol 3 as a nearly equimolar mixture of meso and d,1 dias
meso-Aryl sapphyrins with heteroatoms; synthesis, characterization, spectral and electrochemical properties
Srinivasan, Alagar,Pushpan, Simi K.,Kumar, Murugaeson Ravi,Mahajan, Sumeet,Chandrashekar, Tavarekere K.,Roy, Raja,Ramamurthy
, p. 961 - 968 (2007/10/03)
The synthesis, characterization and spectral properties of six new meso-aryl core modified sapphyrins are described. An efficient approach involving an acid catalyzed condensation of bithiophene diol 1 and modified tripyrranes 2a-2e allows preparation of the desired meso-aryl sapphyrins in 16-36% yield. The product distribution and the isolated yield were found to be dependent on the nature of the acid catalyst (Lewis acid or protic acid) and its concentration. Protic acid catalyst exclusively gave the expected sapphyrins while two additional products, an 18π tetraphenylporphyrin and a 26π modified rubyrin, were isolated under Lewis acid catalysis. An analysis of proton NMR and absorption spectral data suggests that in free base sapphyrins, the heterocyclic ring opposite to the bithiophene unit is inverted as in N-5 meso-aryl sapphyrin and the degree of inversion is dependent on the nature of the heterocyclic ring. The energy optimized structure calculated from the semi-empirical method substantiates such a conclusion. Protonation of sapphyrins generates respective mono- and dications and the heterocyclic ring retains an inverted structure in contrast to normal N-5 sapphyrins. The triplet excited lifetimes for free base and protonated derivatives are similar both under argon saturated and air equilibrated conditions, indicating that the triplet state quenching by oxygen is minimal. Cyclic voltammetric studies reveal easier reductions and harder oxidations relative to meso-aryl porphyrins and the Δredox observed for 3d suggests significant reduction of the HOMO-LUMO energy gap consistent with the large red shift observed for the Soret band.
