Orientation Dependence of Energy Transfer in an Anthracene–Porphyrin Donor–Acceptor System This work was supported by CSIR and DST (New Delhi, India). We thank Dr. T. P. Radhakrishnan for many helpful discussions.

Giribabu, Lingamallu; Kumar, Arunandan; Neeraja, V.; Maiya, Bhaskar G.

doi:10.1002/1521-3773(20011001)40:19<3621::aid-anie3621>3.0.co;2-d

Cited by 54 publications

(24 citation statements)

References 7 publications

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“…It is reasonable to expect that contribution from the PET based mechanism is high for complexes having electron donating axial ligands and it is low for complexes having electron withdrawing axial ligands in this series of tin(IV) porphyrins. This analysis is quite consistent with that made earlier for the analogous series of phosphorus(V) porphyrins [25] and also for the Sn(IV) porphyrin based arrays and other donor-acceptor compounds [22][23][24].…”

Section: Resultssupporting

confidence: 91%

“…axial ligand [12-14, 20-24, 42-45]. As part of our ongoing research program on the metalloid porphyrins [22][23][24][25], we report here the detailed spectroscopic, electrochemical and fluorescence properties of a series of structurally related bis(aryloxo) derivatives of tin(IV) tetra(tolyl) porphyrins.…”

Section: Resultsmentioning

confidence: 99%

“…Our interest in the chemistry of tin(IV) porphyrins originated from the realization that their attractive redox and photochemical properties can be harnessed for performing potentially useful functions [22][23][24]. In this manuscript, we report the details of synthesis, spectral as well as electrochemical characterization and fluorescence properties of a series of tin(IV) porphyrins bearing electron-donating/withdrawing axial aryloxo ligands, Fig.…”

Section: Introductionmentioning

confidence: 99%

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Bis(aryloxo) derivatives of tin(IV) porphyrins: synthesis, spectroscopy and redox activity

Reddy

Maiya

2002

J. Porphyrins Phthalocyanines

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Spectroscopic, electrochemical and fluorescence properties of five octahedral tin(IV) porphyrins ([(TpTP)Sn(O-m,p-C 6 H 3 (CH 3 ) 2 ) 2 ] (1), [(TpTP)Sn(O-p-C 6 H 4 (CH 3 )) 2 ] (2), [(TpTP)Sn(O-C 6 H 5 ) 2 ](3), [(TpTP)Sn(O-p-C 6 H 4 O-o,p-C 6 H 3 (NO 2 ) 2 ) 2 ] (4) and [(TpTP)Sn(O-p-C 6 H 4 (NO 2 )) 2 ] (5)) bearing electron donating/electron withdrawing aryloxo subunits as the axial ligands are investigated in detail. These complexes have been synthesized by the reaction of 5,10,15,20-tetra(4-methylphenyl)porphyrinato tin(IV) dihydroxide ([(TpTP)Sn(OH) 2 ]) and either 3, 4-dimethylphenol, p-cresol, phenol, 4-(2,4dinitrophenoxy)phenol or p-nitrophenol and were isolated in good-to-moderate yields. Analysis of the spectral data (FAB mass, IR, UV-vis and 1 H NMR) of 1 -5 suggests that the two trans axial aryloxo ligands are strongly bound in a symmetric manner at the tin center in these complexes. Specifically, the general symmetry observed in the 1 H NMR spectra and the ring current effect experienced by the protons present on the axial ligands are revealing in this regard. Each porphyrin ring undergoes two successive, reversible/quasi-reversible, one-electron reductions in CH 2 Cl 2 , 0.1 M TBAP. The bound nitroaromatic axial ligands of complexes 4 and 5 could also be reduced under the same set of experimental conditions. The wavelengths of maximum emission, the singlet energies and the Stokes' shifts observed in the fluorescence spectra of 1 -5 are close to the corresponding parameters of the reference porphyrin, [(TpTP)Sn(OH) 2 ]. On the other hand, fluorescence intensities of complexes 1 -4 are quenched in comparison with that of [(TpTP)Sn(OH) 2 ] in three different solvents. A detailed analysis of the emission and redox potential data indicates that a photoinduced electron transfer from the axial aromatic subunit to singlet state of the basal tin(IV) porphyrin can, in principle, explain the fluorescence quenching observed in these donor-acceptor systems. The spectroscopic and redox features of these tin(IV) porphyrins are compared with those of the analogous phosphorus(V) porphyrins reported by us earlier.

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bis(aryloxo) derivatives of tin(IV) porphyrins: synthesis, spectroscopy and redox activity

Reddy

Maiya

2002

J. Porphyrins Phthalocyanines

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“…Because of good spectral overlap, and other photophysical properties, bichromophoric molecules involving anthracene as donor and porphyrins as acceptors have been found to be particularly attractive candidates for studying energy migration, and both covalently bonded [1,[25][26][27] and selfassembled [28] systems of these have been reported. However, whilst much valuable information has been obtained from such studies, our knowledge of processes occurring and the effect of the spacer groups are far from complete.…”

Section: Introductionmentioning

confidence: 99%

Singlet and triplet energy transfer in a bichromophoric system with anthracene covalently linked through sulfonamide to a meso-tetraphenylporphyrin

Melo

Sobral

Gonsalves

2005

Journal of Photochemistry and Photobiology A: Chemistry

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A bichromophoric system in which anthracene has been covalently linked to meso-tetrakis(phenyl)porphyrin (TPP) moieties by alkylsulfonamide spacers has been synthesized and fully characterized. A spectroscopic and photophysical study of this system in dimethylformamide (DMF) has been undertaken to study electronic energy transfer between the anthracene and porphyrin units in excited singlet and triplet states. By use of steady-state and time-resolved fluorescence techniques as well as phosphorescence and laser flash phototolysis, it is shown that excitation to either the singlet or triplet states of the anthracene leads to energy transfer to the lower lying S 1 and T 1 states of TPP group. The efficiency and the rate of energy transfer have been determined. Although the estimated efficiency of the energy transfer process in the singlet manifold is high, the coexistence of fluorescence from both moieties when exciting the anthracene, together with observation of a biexponential decay of the porphyrin fluorescence when excited in the porphyrin Soret band suggest that communication exists between the two chromophores. This is discussed in terms of Förster type energy transfer and geminate radical pair mechanisms, possibly involving nonplanar (between chromophores) excited state geometry. In the flash photolysis studies, only the porphyrin triplet state was observed. The dominance of nonradiative deactivation in the overall decay of the excited singlet and triplet states is indicated.

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“…At first porphyrins were coupled to other tetrapyrrolic chromophores, to carotenes or quinones, in the frame of a biomimetic approach [2][3][4][5], but later they were connected, among others, to metal complexes [6][7][8][9], aromatic hydrocarbons [10][11], bis-imides [12][13] and the fullerenes [14][15][16], with remarkable results.…”

Section: Introductionmentioning

confidence: 99%

A practical approach to the study of photoactive self-assembled porphyrin systems

Flamigni

Talarico

Ventura

2003

J. Porphyrins Phthalocyanines

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An overview of simple methods for the determination, by UV-vis spectroscopy, of association constants of porphyrin based, self-assembling components is presented. Sources of ambiguity and errors are outlined in order to provide non-specialists with basic information. A few cases of self-assembled structures based on porphyrins and displaying photoinduced energy and electron transfer processes are reviewed and evidence is given that a correct determination and interpretation of the association phenomena are of key importance for the interpretation of the photoinduced processes within the array.

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Orientation Dependence of Energy Transfer in an Anthracene–Porphyrin Donor–Acceptor System This work was supported by CSIR and DST (New Delhi, India). We thank Dr. T. P. Radhakrishnan for many helpful discussions.

Cited by 54 publications

References 7 publications

Bis(aryloxo) derivatives of tin(IV) porphyrins: synthesis, spectroscopy and redox activity

Bis(aryloxo) derivatives of tin(IV) porphyrins: synthesis, spectroscopy and redox activity

Singlet and triplet energy transfer in a bichromophoric system with anthracene covalently linked through sulfonamide to a meso-tetraphenylporphyrin

A practical approach to the study of photoactive self-assembled porphyrin systems

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