Influence of Mixed Substituents on the Macrocyclic Ring Distortions of Free Base Porphyrins and Their Metal Complexes

2009 ◽  
Vol 48 (9) ◽  
pp. 3954-3965 ◽  
Author(s):  
P. Bhyrappa ◽  
C. Arunkumar ◽  
B. Varghese
Keyword(s):  
Metal Complexes ◽  
Free Base ◽  
Macrocyclic Ring

scholarly journals Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4351
Author(s):  
Damaris Thuita ◽  
Dinusha Damunupola ◽  
Christian Brückner
Keyword(s):  
Metal Complexes ◽  
Biomedical Applications ◽  
Free Base ◽  
Aryl Group ◽  
Efficient Access ◽  
Metal Derivatives

meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the meso-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, meso-tetraphenylporphyrin (TPP) and meso-tetrakis(pentafluorophenyl)porphyrin (TFPP): free base meso-tetraphenylporpholactone (TPL) and meso-tetrakis(pentafluorophenyl)porpholactone (TFPL), and their platinum(II) and zinc(II) complexes TPLPt, TFPLPt, TPLZn, and TFPLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study.

High pH sensing with water-soluble porpholactone derivatives and their incorporation into a Nafion® optode membrane

The Analyst ◽  
2015 ◽  
Vol 140 (1) ◽  
pp. 190-196 ◽  
Author(s):  
Jill L. Worlinsky ◽  
Steven Halepas ◽  
Masoud Ghandehari ◽  
Gamal Khalil ◽  
Christian Brückner
Keyword(s):  
Metal Complexes ◽  
Water Soluble ◽  
Ph Sensing ◽  
Free Base ◽  
Aryl Group ◽  
High Ph ◽  
Optode Membrane

The known optical high pH sensing chromophores, free base and metal complexes (M = 2H, Zn(ii), Pt(ii)) of meso-tetrakis(pentafluorophenyl)porpholactone, and the as yet untested Ga(iii) complex, were made freely water-soluble by derivatization at the aryl group with PEG chains.

Purpurins Bearing Functionality at the 6,16-meso-Positions: Synthesis From 5,15-Disubstituted meso-[β-(Methoxycarbonyl)vinyl]porphyrins

1990 ◽  
Vol 43 (11) ◽  
pp. 1839 ◽  
Author(s):  
MJ Gunter ◽  
BC Robinson
Keyword(s):  
Cancer Therapy ◽  
Visible Light ◽  
Electronic Spectra ◽  
Potential Application ◽  
Ring Current ◽  
Free Base ◽  
Type B ◽  
Macrocyclic Ring ◽  
Porphyrin Derivatives ◽  
Photodynamic Cancer Therapy

Porphyrins bearing p-X-phenyl substituents (X=Me, OH, OTs , NMe2, NO2) at the 5,15-meso-positions have been synthesized. meso-Formylation of the nickel derivatives produced the derivatives (4), (12), (17) and (23) which show atypical broadened Soret and Q-band absorptions, the latter at 570-750 nm. The optical and n.m.r. spectra of the corresponding free base monoformyl derivatives also indicate electronic perturbations of the porphyrin rr -system. Wittig reactions with ( methoxycarbonylmethylene ) triphenylphosphorane, followed by demetallation, resulted in the meso-acrylate porphyrins (8), (14), (19) and (25), which also exhibit unusual electronic spectra consistent with a distortion of the macrocyclic ring current. The p-dimethylaminophenyl derivative (14) also shows protonation-dependent spectra indicating a quinomethene structure. The meso-acrylate porphyrins were efficiently converted into type A purpurins under basic conditions. Type B purpurins were also formed, and the relative yields of types A and B are temperature and solvent dependent, but independent of the presence of oxygen. These results are in contrast to those for the formation of octaethylpurpurin derivatives; likewise, no evidence of a purpurin - porphyrin equilibrium was observed for these compounds. In the presence of oxygen and strong visible light the meso-formyl-2- ( methoxyoxalyl ) chlorins are formed. The electronic spectra of the purpurins are typified by strong absorptions in the red region of the spectrum; the p- dimethylaminophenyl derivative (27) also exhibits a solvent-dependent spectrum, which is explained in terms of a dimethylaminoquinomethene tautomerism. The purpurins and porphyrin derivatives have potential application in photodynamic cancer therapy.

Synthesis of stable free base secochlorins and their corresponding metal complexes from meso-tetraarylporphyrin derivatives

2012 ◽  
Vol 48 (28) ◽  
pp. 3460 ◽  
Author(s):  
Mamadou Lo ◽  
Jean-François Lefebvre ◽  
Nathalie Marcotte ◽  
Claire Tonnelé ◽  
David Beljonne ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Free Base

Porphyrins, phthalocyanines and related systems in polymer phases

2000 ◽  
Vol 04 (04) ◽  
pp. 418-424 ◽  
Author(s):  
DIETER WÖHRLE
Keyword(s):  
Metal Complexes ◽  
Biological Systems ◽  
Ring Systems ◽  
Macrocyclic Ring

Macrocyclic ring systems in polymer phases described in this overview are part of the field of macromolecular metal complexes. In this review, first, examples of porphyrins in protein environments being active in biological systems are given. These biological sites are essential to understand the functions of artificial systems. Then a classification and examples of synthetic macromolecular metal complexes based on porphyrins, phthalocyanines and related systems are described.

A Structural Parameter to Link Molecular Geometry to Macroscopic Orientation in Discotic Liquid Crystals: Study of Metalloporphyrin Tapes

2021 ◽  
Author(s):  
Yoshiyuki Kobayashi ◽  
Atsuya Muranaka ◽  
Kenichi Kato ◽  
Akinori Saeki ◽  
Takayuki Tanaka ◽  
...  
Keyword(s):  
Liquid Crystals ◽  
Metal Complexes ◽  
Liquid Crystalline ◽  
Molecular Geometry ◽  
Structural Parameter ◽  
Discotic Liquid Crystals ◽  
Free Base ◽  
Base Form ◽  
Macroscopic Orientation

Novel liquid crystalline (LC) molecules were prepared from a triply linked dimeric porphyrin tape. A series of metal complexes (1Zn, 1Pd, 1Cu, and 1Ni) and the free-base form (12H) of...

The Synthesis and Properties of Free‐Base [14]Triphyrin(2.1.1) Compounds and the Formation of Subporphyrinoid Metal Complexes

2011 ◽  
Vol 17 (16) ◽  
pp. 4396-4407 ◽  
Author(s):  
Zhao Li Xue ◽  
John Mack ◽  
Hua Lu ◽  
Lei Zhang ◽  
Xiao Zeng You ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Free Base
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