β,<i>meso</i>‐Acetylenyl‐Bridged, Asymmetrical, Porphyrin Dyads – Synthesis, Spectral, Electrochemical and Computational Studies

Meesala, Yedukondalu; Maity, Dilip Kumar; Ravikanth, Mangalampalli

doi:10.1002/ejoc.200901362

Cited by 14 publications

(5 citation statements)

References 80 publications

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“…For example, the porphyrin dyad 116 containing ZnN 4 porphyrin sub-unit and N 3 S porphyrin sub-unit, on excitation at 550 nm, the emission of ZnN 4 porphyrin quenched by 98% and the strong emission from N 3 S porphyrin sub-unit was observed due to energy transfer from ZnN 4 porphyrin subunit to N 3 S porphyrin sub-unit. 41 Similarly, all unsymmetrical porphyrin dyads 115-121 also showed an energy transfer from donor porphyrin unit to acceptor porphyrin unit as confirmed by steady state fluorescence studies.…”

Section: Ethyne Bridged Unsymmetrical Porphyrin Dyadsmentioning

confidence: 69%

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Mono‐functionalized Heteroporphyrin Building Blocks and Unsymmetrical Covalent and Non‐covalent Porphyrin Dyads

Yedukondalu

Ravikanth

2011

J Chinese Chemical Soc

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Heteroporphyrins resulted from the replacement of one or two pyrrolic nitrogens with other hetero atoms such as O, S, Se and Te possess very interesting and distinct properties compared to tetrapyrrolic porphyrins. Specially, the singlet state energy levels can be fine tuned with suitable modification of porphyrin core by substituting pyrrolic "N" with other hetero atoms such as "O" and "S". In this review, we describe our synthetic approaches for the synthesis of various mono-functionalized heteroporphyrin building blocks and their use in the synthesis of several covalently and non-covalently linked unsymmetrical porphyrin dyads containing two different porphyrin sub-units. The photophysical studies are also described to show the possibility of singlet-singlet energy transfer from one porphyrin sub-unit to another in these unsymmetrical porphyrin dyads.

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Section: Ethyne Bridged Unsymmetrical Porphyrin Dyadsmentioning

confidence: 69%

“…41 The dyads Pd 2 (dba) 3 /AsPh 3 in toluene/triethylamine at 35°C for 4 h (Scheme XII). The metal free dyads 119-121 were synthesized by demetalation of dyads 116-118 respectively by treating the corresponding metalated dyad in CHCl 3 with TFA for 15 min (Scheme XII).…”

Section: Ethyne Bridged Unsymmetrical Porphyrin Dyadsmentioning

confidence: 99%

Mono‐functionalized Heteroporphyrin Building Blocks and Unsymmetrical Covalent and Non‐covalent Porphyrin Dyads

Yedukondalu

Ravikanth

2011

J Chinese Chemical Soc

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“…A series of ethyne-bridged unsymmetrical porphyrin dyads 76 – 77 containing two different porphyrin units were synthesized as shown in Scheme . The β- meso -ethyne-bridged unsymmetrical ZnN 4 –N 2 XY porphyrin dyads 76a – d were synthesized by coupling of β-ethynyl ZnN 4 porphyrin 75 with appropriate meso -bromo heteroporphyrin building block 13a/14a/34a/40a in the presence of Pd 2 (dba) 3 /AsPh 3 in toluene/triethylamine at 35 °C for 3 h. The ethyne-bridged unsymmetrical free base N 4 –N 2 XY porphyrin dyads 77a – c were synthesized by demetalation of appropriate ethyne-bridged ZnN 4 –N 2 XY porphyrin dyads 76a – d with trifluoroacetic acid (TFA) in CHCl 3 followed by simple column chromatographic purification. The fluorescence studies indicated a possibility of energy transfer at the singlet state from donor porphyrin unit to acceptor porphyrin unit in all ethyne-bridged unsymmetrical porphyrin dyads.…”

Section: Covalently and Noncovalently Linked Heteroporphyrin-based Mu...mentioning

confidence: 99%

“…A series of ethyne-bridged unsymmetrical porphyrin dyads 76 purification. The fluorescence studies indicated a possibility of energy transfer at the singlet state from donor porphyrin unit to acceptor porphyrin unit in all ethyne-bridged unsymmetrical porphyrin dyads.…”

Section: Covalently Linked Heteroporphyrin-based Arraysmentioning

confidence: 99%

Heteroatom-Containing Porphyrin Analogues

Shetti²,

et al. 2016

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The heteroatom-containing porphyrin analogues or core-modified porphyrins that resulted from the replacement of one or two pyrrole rings with other five-membered heterocycles such as furan, thiophene, selenophene, tellurophene, indene, phosphole, and silole are highly promising macrocycles and exhibit quite different physicochemical properties compared to regular azaporphyrins. The properties of heteroporphyrins depend on the nature and number of different heterocycle(s) present in place of pyrrole ring(s). The heteroporphyrins provide unique and unprecedented coordination environments for metals. Unlike regular porphyrins, the monoheteroporphyrins are known to stabilize metals in unusual oxidation states such as Cu and Ni in +1 oxidation states. The diheteroporphyrins, which are neutral macrocycles without ionizable protons, also showed interesting coordination chemistry. Thus, significant progress has been made in last few decades on core-modified porphyrins in terms of their synthesis, their use in building multiporphyrin arrays for light-harvesting applications, their use as ligands to form interesting metal complexes, and also their use for several other studies. The synthetic methods available in the literature allow one to prepare mono- and diheteroporphyrins and their functionalized derivatives, which were used extensively to prepare several covalent and noncovalent heteroporphyrin-based multiporphyrin arrays. The methods are also developed to synthesize different hetero analogues of porphyrin derivatives such as heterocorroles, heterochlorins, heterocarbaporphyrinoids, heteroatom-substituted confused porphyrins, and so on. This Review summarizes the key developments that have occurred in heteroporphyrin chemistry over the last four decades.

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“…The yield improved to 55% at 75 ℃ for 6 h, and up to 82% at 85 ℃ (Table 1, Entries 3,4). Further rising temperature will not continuously increase the yield but lead to the increase of by-products (Table 1, Entries 5,6). So 85 ℃ was the better choice of reaction temperature.…”

Section: Resultsmentioning

confidence: 98%

Solvent-Free Aldol Reaction of β-Porphyrin Formaldehyde with Ketone

Zhou¹,

Zhou²,

Jia³

et al. 2019

Chin. J. Org. Chem.

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A convenient approach for the synthesis of β-substituted α,β-unsaturated carbonyl porphyrin compounds via base-catalyzed aldol reaction was developed. By this method, a series of β-substituted α,β-unsaturated carbonyl porphyrin compounds were constructed using β-porphyrin formaldehyde and ketones with moderate to excellent yields under mild reaction conditions, especially solvent-free, and good functional group tolerance. Furthermore, this process was successfully applied to the reactions of different metal porphyrin which have been reported to have poor reaction effects with good yields.

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β,meso‐Acetylenyl‐Bridged, Asymmetrical, Porphyrin Dyads – Synthesis, Spectral, Electrochemical and Computational Studies

Cited by 14 publications

References 80 publications

Mono‐functionalized Heteroporphyrin Building Blocks and Unsymmetrical Covalent and Non‐covalent Porphyrin Dyads

Mono‐functionalized Heteroporphyrin Building Blocks and Unsymmetrical Covalent and Non‐covalent Porphyrin Dyads

Heteroatom-Containing Porphyrin Analogues

Solvent-Free Aldol Reaction of β-Porphyrin Formaldehyde with Ketone

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