Anion Chelation-Induced Porphyrin Protonation and Its Application for Chloride Anion Sensing

Zhang, Ying; Li, Mei Xian; Lu, Ming; Yang, Rui; Liu, Feng; Li, Ke An

doi:10.1021/jp050516a

Cited by 53 publications

(57 citation statements)

References 57 publications

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“…During the process of protonation, the counteranion of the proton source binds to the porphyrin core and thus promotes its protonation. 34 Consequently, a description of the formation of the monoacid and diacid should involve the counteranion X − (Eqs. 4 and 5):…”

Section: Acid-base Behaviormentioning

confidence: 99%

See 1 more Smart Citation

Catalysis of Oxygen Reduction by Metal-Free Porphyrins in One- and Two-Phase Liquid Systems

Samec¹,

Langmaier²,

Trojánek³

et al. 2014

Handbook of Porphyrin Science

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Section: Acid-base Behaviormentioning

confidence: 99%

“…33): (33) should be rapidly converted into the first stable product, i.e., hydrogen peroxide 96 (Eq. 34): (34) …”

Section: A Catalysis Of Oxygen Reduction In Solutionmentioning

confidence: 99%

Catalysis of Oxygen Reduction by Metal-Free Porphyrins in One- and Two-Phase Liquid Systems

Samec¹,

Langmaier²,

Trojánek³

et al. 2014

Handbook of Porphyrin Science

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“…10,11 In the free base Por, four phenyl rings are not conjugated with porphyrin ring because they lie almost perpendicular to the porphyrin plane, whereas in the highly distorted structure of the diprotonated H 2 Por 2+ they rotate towards a more parallel position and have more highly con- 2+ results in redshifted spectrum relative to that of free base Por.…”

Section: +mentioning

confidence: 99%

Solvent-dependent Photoreactions of Porphyrin-Spiropyran Dyad: Ring-opening or Protonation

Hur¹,

Shin

2013

Bulletin of the Korean Chemical Society

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Porphyrin (Por) has a strong absorption characteristics in the range of sunlight due to a chemical structure of high conjugation and rigidity, good redox properties, and wellestablished synthetic methods. Accordingly, porphyrin-based multicomponent compounds have been investigated in a variety of applications such as artificial light-harvesting antenna, molecular energy storage devices, solar cells, optoelectronic switches, and photodynamic therapy. 1-5Spiropyran (SP) is a typical photochromic molecule performing the reversible interconversion between colorless SP and colored merocyanine (MC). UV-absorbing SP is turned into VIS-absorbing MC by the photochemical ring opening reaction on UV irradiation. Reversely, MC is transformed to SP by the thermal or visible light-induced ring closing reaction. Reversible SP-MC transformation is one of subjects of active research on optical memory and switch in a point of view that the polarity, the excited state energy, or molecular geometry of SP and MC are significantly different. 6-8It is expected that the combination of photoactive Por and photochromic SP could lead to an interesting light-controllable molecular device to control on-off switching of photoinduced processes.In this work, Por-SP dyad linked by ester linkage was prepared by the esterification reaction between carboxylic acid-functionalized porphyrin and hydroxy-functionalized spiropyran and its photoinduced transformation was investigated in tetrahydrofuran and dichloromethane. For Por-SP in tetrahydrofuran, the porphyrin Soret-band maximum is at 416 nm, the porphyrin Q-band maxima are at 515, 550, 590, 645 nm and absorption of spiropyran appears at 350 nm.On irradiation at 350 nm, the absorption spectral changes of Por-SP in tetrahydrofuran were measured with the irradiation time in 5-seccond intervals for 40 sec (Figure 1). Porphyrin characteristic bands at 416 (Soret band), 515, 550, 645 (Q bands) nm remain unchanged, but only the absorbance in 590 nm region corresponding to merocyanine absorption has increased as spiropyran moiety carries out the photochemical ring opening reaction to merocyanine. In tetrahydrofuran, Por-SP is photochemically transformed into Por-MC. These are the same results as reported previously for Porphyrin-Spiropyran dyad linked by methylene linkage.9 As shown in inset of Figure 1, complete conversion from Por-SP into Por-MC takes ~25 sec. Solution colour changes from red to violet. These spectral features are similar to those of diprotonated H 2 Por 2+, formed by the addition of acid to free base Por where two pyrrole imine nitrogens in the core accept two protons.10,11 In the free base Por, four phenyl rings are not conjugated with porphyrin ring because they lie almost perpendicular to the porphyrin plane, whereas in the highly distorted structure of the diprotonated H 2 Por 2+ they rotate towards a more parallel position and have more highly con-

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“…, where two pyrrole imine nitrogens in the core accept two protons. 27,28 In this case, core nitrogens in rotaxane 4 may be protonated by HCl production from the porphyrin-catalyzed photodecomposition of dichloromethane. Figure 2 shows absorption and fluorescence spectra of rotaxane 5 with those of zinc porphyrin-benzene-zinc porphyrin 2 and viologen derivative 3 in dichloromethane.…”

mentioning

confidence: 99%

Rotaxane Based on Bis-Porphyrin Threaded onto Bis-Viologen Macrocycle

Shin¹

2014

Rapid Communication in Photoscience

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Rotaxanes have been prepared using benzenelinked bis-porphyrin or bis-zinc porphyrin as a string component and bis-viologen as a macrocyclic ring component. Absorption and fluorescence spectra of rotaxane formed by complexation of two components have been investigated.Construction of some interlocked molecules, such as pseudorotaxanes, rotaxanes, and catenanes may be considered as one of the most useful tools for preparing the functional synthetic molecular-level nanomachines or switches.1-11 When the proper chemical or physical stimuli are used, their interlocked structures allow tunable translational motion at the nanoscale. The mechanical movements of movable components from the stationary components in molecular machine may be induced in response to some external stimulus such as pH, chemical, electrical energy, or light. In turn, some observable properties such as absorption or luminescence are switched on/off and thereby opening up the way to process information at the molecular level.Rotaxanes 12 consisting of ring and string fragments have been very accessible compounds by the many efficient template synthesis studied since 1980s. The template-directed synthetic strategies reliant on pi-electron donor-acceptor interactions, transition metal complexation, and steric fit/hydrogen bonding have not only made the synthesis of rotaxanes more accessible but have also allowed the preparation of compounds incorporating chemically, electrochemically, and photochemically accessible functionalities. They play a role as building blocks for molecular-scale electronic and photonic devices. Recently, a wide variety of rotaxanes with different strings and macrocyclic rings have been developed for different applications.Among external stimuli activating the molecular machine, light has many advantages such as no generation of waste products, rapid on/off switching, and easy monitoring. 13 In terms of building light-controllable molecular machine, it is interesting to introduce photo-active components such as porphyrin and viologen into the supramolecular interlocked molecules including rotaxanes.Porphyrins are strong visible light absorbing molecules and frequently employed as electron donor in multicomponent electron transfer systems. Benzene is used as a linker as well -electron donor. Positively charged viologen is a typical electron acceptor. Moreover, many positively charged rotaxanes have been prepared by self--stacked interaction between viologen and aromatic compound. [14][15][16] In supramolecule composed of porphyrin and viologen or other electron acceptor, it is expected that visible irradiation leads to the generation of excited porphyrin and then photoinduced electron transfer from excited porphyrin to viologen or other electron acceptor.17,18 Light-induced redox reaction of viologen moiety may apply to derive the lighttriggered translocation of molecular components in rotaxanes.19 While many rotaxanes 20 and pseudorotaxanes 21 containing both porphyrin and viologen have been studied, rotaxanes cons...

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Anion Chelation-Induced Porphyrin Protonation and Its Application for Chloride Anion Sensing

Cited by 53 publications

References 57 publications

Catalysis of Oxygen Reduction by Metal-Free Porphyrins in One- and Two-Phase Liquid Systems

Catalysis of Oxygen Reduction by Metal-Free Porphyrins in One- and Two-Phase Liquid Systems

Solvent-dependent Photoreactions of Porphyrin-Spiropyran Dyad: Ring-opening or Protonation

Rotaxane Based on Bis-Porphyrin Threaded onto Bis-Viologen Macrocycle

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