66951-03-9

Upstream product

• 288-05-1 selenophene 
• 100-52-7 benzaldehyde 
• 17338-03-3 1,6-diphenylhexa-2,4-diyne-1,6-diol 

Downstream Products

• 66951-07-3 2,4,6,8-tetraphenyl-1,5(2,5)-dipyrrola-3(2,5)-selenophena-7(2,5)-thiophena-cyclooctaphane-1⁽²⁾,4,6,7⁽⁸⁾-tetraene 

Relevant academic research and scientific papers

Synthesis of Selenium and Tellurium Core-Modified Azuliporphyrinogens and Benziporphyrinogens and Corresponding Carbaporphyrinoids

The synthesis of selenium and tellurium core-modified carbaporphyrinogens was carried out by the reaction of functional selenophene/tellurophene diols with azulene or a benzitripyrrane in the presence of acid. The products were obtained in moderate yields and were characterized by using 1H and 13C NMR, UV-vis, FT-IR, CV, and HRMS spectroscopic techniques. Further, oxidation of the obtained core-modified carbaporphyrinogens in the presence of DDQ in CHCl3 afforded the corresponding carbaporphyrins in good yields. Benziporphyrins showed no indication of a ring current or macrocyclic aromaticity as confirmed by using proton NMR spectroscopy, but the addition of TFA gave rise to the formation of weakly diatropic dications.

Synthesis of 21,23-selenium- and tellurium-substituted 5-porphomethenes, 5,10-porphodimethenes, 5,15-porphodimethenes, and porphotrimethenes and their interactions with mercury

The 3+1 condensation of symmetrical 16-Selena/telluratripyrranes with symmetrical selenophene-2,5-diols/tellurophene-2,5-diols in the presence of BF3-etheratre or BF3-methanol followed by oxidation with DDQ gave 5,10-porphodimethenes, whereas the process with unsymmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave 5-porphomethenes. In addition, the reaction of unsymmetrical 16-Selena/telluratripyrranes with symmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave the corresponding porphotrimethenes, whereas the process with unsymmetrical selenophene-2,5-diols/tellurophene-2,5-diols gave the 5,15-porphodimethenes. The structures of different products were characterized by IR, 1H and 13C NMR, 1H-1H COSY, CHN analysis, and mass spectrometry. The binding of mercury with the calix[4]phyrins mentioned above had been observed in the decreasing order of porphodimethenes > porphomethenes > porphotrimethenes by UV-vis and 1H NMR spectroscopy.

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)

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.

Synthesis and properties of fused-ring-expanded porphyrins that were core-modified with Group 16 heteroatoms

The synthesis of a series of novel core-modified and fused-ring-expanded tetraphenylporphyrins is reported. Theoretical calculations and magnetic circular dichroism (MCD) and fluorescence spectroscopic measurements were used to analyze the effect of core modification with Group 16 oxygen, sulfur, selenium, and tellurium atoms on the optical properties and electronic structures of the porphyrins. Marked redshifts of the Q and B bands and accelerated intersystem-crossing rates were observed, thus making these compounds potentially suitable for use in a variety of applications. The scope for further fine-tuning of these optical properties based on additional structural modifications, such as the incorporation of fused benzene rings to form ABAB structures by using a thiophene precursor with a fused bicyclo[2.2.2]octadiene ring and the introduction of various substituents onto the meso-phenyl rings, is also examined. Core-modified porphyrinoids: The synthesis of a series of novel core-modified and fused-ring-expanded tetraphenylporphyrins is reported (see figure). Theoretical calculations, magnetic circular dichroism (MCD), and fluorescence emission spectroscopy are used to analyze the effect of core modification with Group 16 oxygen, sulfur, selenium, and tellurium atoms on the optical properties and electronic structures. Copyright

Water soluble, core-modified porphyrins. 3. Synthesis, photophysical properties, and in vitro studies of photosensitization, uptake, and localization with carboxylic acid-substituted derivatives

Water soluble, core-modified porphyrins 1-5 bearing 1-4 carboxylic acid groups were prepared and evaluated in vitro as photosensitizers for photodynamic therapy. The 21,23-core-modified porphyrins 1-5 gave band I absorption maxima with λmax of

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

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

Water-soluble, core-modified porphyrins as novel, longer-wavelength- absorbing sensitizers for photodynamic therapy

Water-soluble, core-modified 5,10,15,20-tetrakis(4-sulfonatophenyl)- 21,23-dithiaporphyrin (1) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23- diselenaporphyrin (2) were prepared as the tetrasodium salts by the sulfonation of 5,10,15,20-tetraphenyl-21,2

Novel core-modified expanded porphyrins with meso-Ary1 substituents: Synthesis, spectral and structural characterization

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