A new synthetic route to donor–acceptor porphyrins

Plater, M. John; Aiken, Stuart; Bourhill, Grant

doi:10.1016/s0040-4020(02)00109-6

Cited by 86 publications

(65 citation statements)

References 25 publications

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“…[14][15][16][17][18] Four strong electron withdrawing pentafluoroaryl rings at the meso-carbon atoms of tetra-fluoroarylporphyrins endowed with relatively bulkier fluorine atoms make these porphyrins quite different from tetraphenyl/tetratolylporphyrins in their physical properties and chemical activities. [19][20][21][22] The synthesis of the donor-acceptor porphyrins was performed using a new converging approach, which differs from the procedures originally described by Therien 23 and later used by Plater 24 for the preparation of other arylethynyl porphyrins. Porphyrins have been of great scientific interest due to their involvement in the photosynthetic reaction centers and hemeproteins.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

Rajesh¹,

Rahiman²,

Bharathi³

et al. 2010

Bulletin of the Korean Chemical Society

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We have synthesized a series of push-pull porphyrins containing both donor and acceptor substituents at the mesopositions and have examined their spectral and biological properties. The push-pull porphyrins containing both strong donor NH2 and acceptor NO2 at meso-positions, in which donor group condensed with the ligand, (2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol (L) to form imine linkages with porphyrin. The Schiff base ligand 5-[4-(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethylphenol)phenyl]-10,15,20-tris(4-nitrophenyl) porphyrin [an3(TPP)L] can be synthesized from 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) and 5-(4-aminophenyl)-10, 15,20-tris(4-nitrophenyl)porphyrin. The push-pull porphyrin [an3(TPP)L] was metallated to get copper, nickel and zinc complexes. The spectral, electrochemical, antibacterial, antifungal and cytotoxicity properties of all the donor-acceptor push-pull porphyrins and their complexes were characterized and studied.

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Section: Introductionmentioning

confidence: 99%

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

Rajesh¹,

Rahiman²,

Bharathi³

et al. 2010

Bulletin of the Korean Chemical Society

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“…[10] In the first step, a trimethylsilylacetyl-substituted N 3 S porphyrin derivative of 3 was prepared in 78 % yield by treating 2 Scheme 1. Synthetic scheme for the preparation of meso-bromo-21-thiaporphyrin 2.…”

Section: Resultsmentioning

confidence: 99%

meso‐5‐Bromo‐10,15,20‐tri(p‐tolyl)‐21‐thiaporphyrin as a Precursor for the Synthesis of Novel Compounds

Punidha¹,

Agarwal²,

Gupta³

et al. 2007

Eur J Org Chem

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The synthesis of eight novel compounds with meso‐5‐bromo‐10,15,20‐tri(p‐tolyl)‐21‐thiaporphyrin as a key synthon under mild Pd‐coupling conditions is reported. The title compound was prepared easily by treating the readily available 10,15,20‐tri(p‐tolyl)‐21‐thiaporphyrin with N‐bromosuccinimide at room temperature for 10 min. The use of the title compound was demonstrated by synthesizing 21‐thiaporphyrin‐based complex systems such as ethyne‐bridged N3S‐N3S dyad, phenylethyne‐bridged N3S‐N3O dyad, N3S‐N2S2 dyad, meso‐meso‐linked ZnN4‐N3S dyad and ZnN4‐N3S‐ZnN4 triad under mild Pd‐mediated coupling conditions. The steady‐state fluorescence studies indicated a possibility of an efficient energy transfer between the two porphyrin subunits in the dyads and triad. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…3,5-Di-tert-butylbenzaldehyde and meso-[3,5-di-(tert-butyl)phenyl]dipyrromethane were synthesized by following procedures reported in the literature. [33,34] 10-N-Decylisoalloxazine (DecFl) was prepared in a similar procedure to that described in the literature.…”

Section: Experimental Section Generalmentioning

confidence: 99%

Binding of Scandium Ions to Metalloporphyrin–Flavin Complexes for Long‐Lived Charge Separation

Kojima

Kobayashi

Ishizuka

et al. 2014

Chemistry A European J

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A porphyrin-flavin-linked dyad and its zinc and palladium complexes (MPor-Fl: 2-M, M=2 H, Zn, and Pd) were newly synthesized and the X-ray crystal structure of 2-Pd was determined. The photodynamics of 2-M were examined by femto- and nanosecond laser flash photolysis measurements. Photoinduced electron transfer (ET) in 2-H2 occurred from the singlet excited state of the porphyrin moiety (H2 Por) to the flavin (Fl) moiety to produce the singlet charge-separated (CS) state (1) (H2 Por(.+) -Fl(.-) ), which decayed through back ET (BET) to form (3) [H2 Por]*-Fl with rate constants of 1.2×10(10) and 1.2×10(9) s(-1) , respectively. Similarly, photoinduced ET in 2-Pd afforded the singlet CS state, which decayed through BET to form (3) [PdPor]*Fl with rate constants of 2.1×10(11) and 6.0×10(10) s(-1) , respectively. The rate constant of photoinduced ET and BET of 2-M were related to the ET and BET driving forces by using the Marcus theory of ET. One and two Sc(3+) ions bind to the flavin moiety to form the Fl-Sc(3+) and Fl-(Sc(3+) )2 complexes with binding constants of K1 =2.2×10(5) M(-1) and K2 =1.8×10(3) M(-1) , respectively. Other metal ions, such as Y(3+) , Zn(2+) , and Mg(2+) , form only 1:1 complexes with flavin. In contrast to 2-M and the 1:1 complexes with metal ions, which afforded the short-lived singlet CS state, photoinduced ET in 2-Pd⋅⋅⋅Sc(3+) complexes afforded the triplet CS state ((3) [PdPor(.+) -Fl(.-) (Sc(3+) )2 ]), which exhibited a remarkably long lifetime of τ=110 ms (kBET =9.1 s(-1) ).

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A new synthetic route to donor–acceptor porphyrins

Cited by 86 publications

References 25 publications

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

meso‐5‐Bromo‐10,15,20‐tri(p‐tolyl)‐21‐thiaporphyrin as a Precursor for the Synthesis of Novel Compounds

Binding of Scandium Ions to Metalloporphyrin–Flavin Complexes for Long‐Lived Charge Separation

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