116123-17-2Relevant academic research and scientific papers
Spiropyran-based photoswitchable dimethylaminopyridine
Zhou, Tao,Li, Zhihao,Wang, Jiaobing
, p. 8869 - 8872 (2019)
Embedding of DMAP in a spiropyran derivative results in a molecular switch 1, which changes the coordination capability of the DMAP moiety upon exposure to external stimuli such as light and heat. In the closed form, 1c behaves as an isolated DMAP, complexing with zinc porphyrin (ZnP) with a high binding constant (K = 1.8 × 104 M-1). However, in the open form, 1o associates with ZnP with a much weaker binding strength (K = 0.5 × 104 M-1). Switching between 1c and 1o is fast and reversible. In the photostationary state under irradiation at 330 nm, 90% of 1 is transformed from 1c to 1o.
Cunning metal core: Efficiency/stability dilemma in metallated porphyrin based light-emitting electrochemical cells
Weber, Katharina T.,Karikis, Kostas,Weber, Michael D.,Coto, Pedro B.,Charisiadis, Asterios,Charitaki, Despina,Charalambidis, Georgios,Angaridis, Panagiotis,Coutsolelos, Athanassios G.,Costa, Rubén D.
, p. 13284 - 13288 (2016/09/04)
The syntheses, photophysical/electrochemical characterizations of different metallated porphyrins-i.e., Zn2+, Pt2+, Pd2+, and Sn4+ porphyrins-as well as their first application in light-emitting electrochemical cells are provided. A direct comparison demonstrates that depending on the metallation either efficient (Pt-por) or stable (Zn-por) devices are achieved, demonstrating that the choice of the metal core is a key aspect for future developments.
A Lewis acid-mediated conformational switch
Knipe, Peter C.,Lingard, Hannah,Jones, Ian M.,Thompson, Sam,Hamilton, Andrew D.
supporting information, p. 7937 - 7941 (2015/01/08)
Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an iso
Tetraaryl ZnII porphyrinates substituted at β-pyrrolic positions as sensitizers in dye-sensitized solar cells: A comparison with meso-disubstituted push-pull ZnII porphyrinates
Di Carlo, Gabriele,Orbelli Biroli, Alessio,Pizzotti, Maddalena,Tessore, Francesca,Trifiletti, Vanira,Ruffo, Riccardo,Abbotto, Alessandro,Amat, Anna,De Angelis, Filippo,Mussini, Patrizia R.
supporting information, p. 10723 - 10740 (2013/08/23)
A facile and fast approach, based on microwave-enhanced Sonogashira coupling, has been employed to obtain in good yields both mono- and, for the first time, disubstituted push-pull ZnII porphyrinates bearing a variety of ethynylphenyl moieties at the β-pyrrolic position(s). Furthermore, a comparative experimental, electrochemical, and theoretical investigation has been carried out on these β-mono- or disubstituted ZnII porphyrinates and meso-disubstituted push-pull ZnII porphyrinates. We have obtained evidence that, although the HOMO-LUMO energy gap of the meso-substituted push-pull dyes is lower, so that charge transfer along the push-pull system therein is easier, the β-mono- or disubstituted push-pull porphyrinic dyes show comparable or better efficiencies when acting as sensitizers in DSSCs. This behavior is apparently not attributable to more intense B and Q bands, but rather to more facile charge injection. This is suggested by the DFT electron distribution in a model of a β- monosubstituted porphyrinic dye interacting with a TiO2 surface and by the positive effect of the β substitution on the incident photon-to-current conversion efficiency (IPCE) spectra, which show a significant intensity over a broad wavelength range (350-650 nm). In contrast, meso-substitution produces IPCE spectra with two less intense and well-separated peaks. The positive effect exerted by a cyanoacrylic acid group attached to the ethynylphenyl substituent has been analyzed by a photophysical and theoretical approach. This provided supporting evidence of a contribution from charge-transfer transitions to both the B and Q bands, thus producing, through conjugation, excited electrons close to the carboxylic anchoring group. Finally, the straightforward and effective synthetic procedures developed, as well as the efficiencies observed by photoelectrochemical measurements, make the described β-monosubstituted ZnII porphyrinates extremely promising sensitizers for use in DSSCs. Copyright
[2]Catenanes decorated with porphyrin and [60]fullerene groups: Design, convergent synthesis, and photoinduced processes
Megiatto Jr., Jackson D.,Schuster, David I.,Abwandner, Silke,De Miguel, Gustavo,Guldi, Dirk M.
experimental part, p. 3847 - 3861 (2010/05/15)
A new class of [2]catenanes containing zinc(II)-porphyrin (ZnP) and/or [60]fullerene (C60) as appended groups has been prepared. A complete description of the convergent synthetic approach based on Cu(I) template methodology and "click" 1, 3-di
Formyl-Porphyrln and formyl-fullerenoporphyrln building blocks for the construction of multlporphyrln arrays
Urbani, Maxence,Iehl, Julien,Osinska, Iwona,Louis, Remy,Holler, Michel,Nierengarten, Jean-Francois
experimental part, p. 3715 - 3725 (2009/12/05)
A Eullerene derivative bearing a benzaldehyde unit has been prepared and used as starting material for the synthesis of a formyl-fullerenoporphyrin building block. Condensation of this aldehyde with pyrrole in CHCl3 with BF3·Et2O as catalyst followed by p-chloranil oxidation yielded a pentaporphyrinic scaffold surrounded by four peripheral C60 subunits. By following a similar strategy, a bis-porphyrin building block bearing an aldehyde function was prepared and used for the construction of a nonaporphyrin array by reaction with pyrrole under typical porphyrin synthesis conditions. Whereas the 1H NMR spectrum recorded at room temperature for the nonaporphyrin system is well defined, the signals recorded under the same conditions for the pentaporphyrin derivative surrounded by four peripheral C60 groups are broad. Indeed, the C 60-pentaporphyrin ensemble appears as a mixture of conformers which equilibrate slowly on the NMR time scale at room temperature.
Complex formation of tetra(3,5-di-tert-butylphenyl)porphine with copper(II) and zinc(II) acetates in organic solvents
Berezin,Berezin,Syrbu
, p. 335 - 340 (2009/12/25)
The effect of accumulation of the tert-butyl groups in the phenyl rings of tetraphenylporphine on the complex formation rate of tetra(3,5-di-tert- butylphenyl)porphine (I) with copper(II), zinc(II), and cadmium(II) acetates in acetic acid and in a mixed e
Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers
Bakar, Mohd Bakri,Oelgem?ller, Michael,Senge, Mathias O.
experimental part, p. 7064 - 7078 (2009/12/06)
Photodynamic therapy (PDT) selectivity and specificity can be improved by binding the photosensitizers to target receptors. One approach is to cross-link porphyrins to a biological target receptor via the photocleavable o-nitrobenzyl linker, where a contr
Thermal study of metalloporphyrin complexes with benzene
Balantseva,Antina,Berezin,V'Yugin
, p. 1566 - 1570 (2008/10/09)
The crystal solvates of the complexes MP (P is the dianion of tetrakis(3,5-di-tert-butylphenyl)porphine, M = Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II)) and (Ac)MnP with benzene were obtained by isothermal evaporation of corresponding solutions at 35°C. Their thermal decomposition was studied. The compositions of the crystal solvates and the temperature and enthalpy of evaporation of benzene from them were determined. The π system of the macrocyclic ring in the metalloporphyrins was found to act as the π donor with respect to the aromatic system of the benzene molecule. Copyright
