- Synthesis and properties of fused-ring-expanded porphyrins that were core-modified with Group 16 heteroatoms
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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
- Xu, Hai-Jun,MacK, John,Wu, Di,Xue, Zhao-Li,Descalzo, Ana B.,Rurack, Knut,Kobayashi, Nagao,Shen, Zhen
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p. 16844 - 16867
(2013/03/28)
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- Synthesis, characterization, and anti-amoebic screening of core-modified 5,20-bis{2-{[(alkyl)(alkyl′)amino]methyl}ferrocen-1-yl}-10,15-diphenyl-21, 23-dithiaporphyrin (=1,1″-(10,15-diphenyl-21,23-dithiaporphine-5,20-diyl) bis[2-{[(alkyl)(alkyl′)amino]methyl}ferrocene]) derivatives
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The synthesis of the first bis-ferrocenyl-substituted core-modified porphyrins, 5,20-bis{2-{[(alkyl)-(alkyl′)amino]methyl}ferrocen-1-yl}-10, 15-diphenyl-21,23-dithiaporphyrin derivatives 6a - 6j, via a multistep route is reported (Schemes 1, 2, and 4). The synthesis was carried out through acid-catalyzed (BF3 ? Et2O) condensation of 1,1″- [thiophene-2,5-diylbis(hydroxymethyl)]bis[2-{[(alkyl)(alkyl′)amino]methyl} ferrocenes] 4a - 4j with 2,2′-[thiophene-2,5-diylbis(phenylmethylene)] bis[1H-pyrrole] (5b) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (=4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; DDQ). Characterization of the compounds was done at each step by means of various spectroscopic techniques. The final compounds were screened for in vitro anti-amoebic activity against the strain HM1:IMSS of E. histolytica (Table 2).
- Bhat, Abdul R.,Bhat, Asif I.,Athar, Fareeda,Azam, Amir
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experimental part
p. 1644 - 1656
(2009/10/16)
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- cis-Pyridyl core-modified porphyrins for the synthesis of cationic water-soluble porphyrins and unsymmetrical non-covalent porphyrin arrays
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Synthesis of a series of 21-thia and 21-oxoporphyrin building blocks containing two pyridyl functional groups at the meso positions in a cis fashion is reported. The building blocks were used to synthesize a series of cationic water-soluble 21-thia and 21-oxoporphyrins. An unsymmetrical non-covalent trimer containing two dissimilar porphyrin cores such as one N3S and two N4 porphyrins cores was also constructed using the pyridyl porphyrin building blocks reported here.
- Santra, Sangita,Kumaresan, Duraisamy,Agarwal, Neeraj,Ravikanth, Mangalampalli
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p. 2353 - 2362
(2007/10/03)
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- Water soluble, core-modified porphyrins. 3. Synthesis, photophysical properties, and in vitro studies of photosensitization, uptake, and localization with carboxylic acid-substituted derivatives
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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
- You, Youngjae,Gibson, Scott L.,Hilf, Russell,Davies, Sherry R.,Oseroff, Allan R.,Roy, Indrajit,Ohulchanskyy, Tymish Y.,Bergey, Earl J.,Detty, Michael R.
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p. 3734 - 3747
(2007/10/03)
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- 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
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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
- 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.
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p. 449 - 461
(2007/10/03)
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- Water-soluble, core-modified porphyrins as novel, longer-wavelength- absorbing sensitizers for photodynamic therapy
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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
- Stilts, Corey E.,Nelen, Marina I.,Hilmey, David G.,Davies, Sherry R.,Gollnick, Sandra O.,Oseroff, Allan R.,Gibson, Scott L.,Hilf, Russell,Detty, Michael R.
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p. 2403 - 2410
(2007/10/03)
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- Synthesis of pseudoaromatic expanded porphyrin analogues
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Optically active expanded porphyrins bearing thiophene were synthesized by Schiff base forming reaction. The condensation of thiophene containing 1,14-bisformyl tripyrrane with aromatic diamines failed to give desired macrocycles but condensation with aliphatic 1,2-diamines gave the desired products. The macrocycles synthesized tend to maintain 18π system and the ethylene bridge shows somewhat resistance toward oxidation.
- Lee,Oh
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p. 1921 - 1924
(2007/10/03)
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- Synthesis of meso-tetraphenylthiaporphyrins bearing one inverted pyrrole
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2-Aza-21-thia-23-carba-5,10,15,20-tetraphenylporphyrin and its N-methylated analogue were synthesized and characterized. The synthesis utilizers [3+1] condensation of thiatripyrrin with 2,4-bis(α-hydroxy-α-phenylmethyl)pyrrole or 2,4-bis(α-hydroxy-α-pheny
- Lee, Chang-Hee,Kim, Han-Je
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p. 3935 - 3938
(2007/10/03)
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