Construction of building blocks for extended porphyrin arrays by nitration of porphyrin-2,3-diones and quinoxalino[2,3-b]porphyrins

Crossley, Maxwell J.; Sheehan, Catherine; Khoury, Tony; Reimers, Jeffrey R.; Sintic, Paul J.

doi:10.1039/b712643c

Cited by 30 publications

(22 citation statements)

References 40 publications

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“…Tetraphenylporphyrin-2,3-dione 4 was prepared from tetraphenylporphyrin applying the literature known methods and obtained 25% in four steps. 30,31 FbTPPNDI was achieved by the condensation of the ortho-diamine NDI 3 with 4 in DCM/pyridine at 45 1C yielding 1 in 89% yield as a purple solid. Finally ZnTPPNDI 2 was achieved in 96% yield by metallation of 1 with using Zn(OAc) 2 in CHCl 3 /MeOH at room temperature.…”

Section: Experimental Section Samplesmentioning

confidence: 99%

Ultrafast excited-state dynamics of strongly coupled porphyrin/core-substituted-naphthalenediimide dyads

Banerji

Bhosale

Petkova

et al. 2011

Phys. Chem. Chem. Phys.

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The photophysics and excited-state dynamics of two dyads consisting of either a free-base or a zinc-tetraphenylporphyrin linked through a rigid bridge to a core-substituted naphthalenediimide (NDI) have been investigated by femtosecond-resolved spectroscopy. The absorption and fluorescence spectra differ substantially from those of the individual units, pointing to a substantial coupling and to a delocalisation of the excitation over the whole molecule, as confirmed by quantum chemistry calculations. A strong dependence of their excited-state dynamics on the solvent polarity has been observed. In toluene, the fluorescence quantum yield of the dyads is of the order of a few percent and the main decay channel of the emitting state is proposed as intersystem-crossing to the triplet state. However, in a medium polarity solvent like dichloromethane, the emitting state undergoes charge separation from the porphyrin to the NDI unit within 1-3 ps, and the ensuing charge-separated state recombines in about 10-20 ps. This solvent dependence can be explained by the weak driving force for charge separation in polar solvents and the large electronic coupling between the porphyrin and NDI moieties, making charge separation a solvent-controlled adiabatic process.

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Section: Experimental Section Samplesmentioning

confidence: 99%

Ultrafast excited-state dynamics of strongly coupled porphyrin/core-substituted-naphthalenediimide dyads

Banerji

Bhosale

Petkova

et al. 2011

Phys. Chem. Chem. Phys.

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“…The precursor zinc( ii ) nitroporphyrin-2,3-dione 1 was prepared according to the method published elsewhere. 109 Following the imidazole-forming condensation method developed earlier, 110 zinc( ii ) nitroporphyrin-dione 1 was reacted with an excess of terephthalaldehyde (5 eq.) in the presence of ammonium acetate in refluxing CHCl 3 and gave zinc( ii ) formyl-imidazoporphyrin 2 in 90% yield.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis 109 and characterization of: zinc( ii ) 12/13-nitro{(formylphenyl)imidazo}porphyrin 2 , 12/13-nitro{(fullerene- N -methylpyrrolidinylphenyl)imidazo}porphyrin 3 , {6′-(3,4-diaminobenzene)quinoxalino}{(fullerene- N -methylpyrrolidinylphenyl)imidazo}porphyrin 5 , (12/13-nitroquinoxalino)(fullereneimidazo)quinoxalino}bisporphyrin 7 , (Tröger's base-quinoxalino){(fullereneimidazo)quinoxalino}trisporphyrin (2HP) 2 Q-Q2HP-C 60 , and (di-zinc( ii ) Tröger's base-quinoxalino){(fullereneimidazo)quinoxalino}trisporphyrin (ZnP) 2 Q-Q2HP-C 60 is described in detail in ESI Section S1 †…”

Section: Methodsmentioning

confidence: 99%

Synthetically tuneable biomimetic artificial photosynthetic reaction centres that closely resemble the natural system in purple bacteria

et al. 2016

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“…The linking of porphyrins at their b,b′-pyrrole positions is a first step in preparing porphyrin modular units as building blocks towards a porphyrinbased molecular wire [4,15,16]. The synthetic flexibility afforded by functionalizing the porphyrin b-pyrrolic periphery as well as the ability to selectively metalate constituent macrocycles [4,[17][18][19][20][21] offers the possibility to create molecules with pre-designed molecular functionality. b,b′-appended and linked porphyrins have been proposed as key components for applications in the area of molecular switches [12], rectifiers [22], solar cells [23] and in long-distance electron-transfer [24,25].…”

Section: Introductionmentioning

confidence: 99%

Electrochemistry of mono- and bis-porphyrins containing a β,β′-fused tetraazaanthracene group

Zhu

Sintic

et al. 2012

J. Porphyrins Phthalocyanines

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Electrochemical and thin-layer spectroelectrochemical properties of mono-and bisporphyrins containing a b,b′-fused tetraazaanthracene (TA) group were examined in CH 2 Cl 2 , PhCN and pyridine containing 0.1 M tetra-n-butylammonium perchlorate as supporting electrolyte. The investigated mono-porphyrins are represented as (PTA)M, where M = 2H, Cu(II) or Zn(II) and PTA = the dianion of 5,10,15,20-tetrakis-(3,5-di-tert-butylphenyl)-6′,7′-dimethyl-1′,4′,5′,8′-tetraazaanthraceno-[2′,3′b]-porphyrin, while the bis-porphyrins are represented by M(P)-TA-(P)M, where M is H 2 , Cu(II), Zn(II), Ni(II) or Pd(II) and P is the dianion of 5,10,15,20-tetrakis-(3,5-di-tert-butylphenyl)porphyrin. The effect of the fused TA group on the redox potentials and UV-visible spectra of the neutral, electroreduced and electrooxidized porphyrins is discussed and the data compared to what is observed for related monoand bis-quinoxalinoporphyrins of the type (PQ)M and (QPQ)M, where Q is a b,b′-fused quinoxaline group. Each TA-linked bis-porphyrin exhibits a strong interaction between the two equivalent porphyrin macrocycles, the magnitude of which is dependent upon the specific metal ion.

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Construction of building blocks for extended porphyrin arrays by nitration of porphyrin-2,3-diones and quinoxalino[2,3-b]porphyrins

Cited by 30 publications

References 40 publications

Ultrafast excited-state dynamics of strongly coupled porphyrin/core-substituted-naphthalenediimide dyads

Ultrafast excited-state dynamics of strongly coupled porphyrin/core-substituted-naphthalenediimide dyads

Synthetically tuneable biomimetic artificial photosynthetic reaction centres that closely resemble the natural system in purple bacteria

Electrochemistry of mono- and bis-porphyrins containing a β,β′-fused tetraazaanthracene group

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