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photophysical properties of corrole

Biju Basumatary, R V Ramana Reddy, Rahul, Jeyaraman Sankar
An expanded porphyrinoid has been obtained by a simple ring expansion from a contracted porphyrinoid, namely corrole. Spectroscopic, structural, and computational investigations reveal peculiar π-conjugation and geometry. The effect of extended π-conjugation is evident from perturbed redox behavior and photophysical properties. Owing to the strong diatropic ring current of the corrole and cross-conjugation, the molecule exhibits a non-aromatic nature for the expanded π-circuit, as evident from NMR studies...
March 5, 2018: Angewandte Chemie
Julia Preiß, Felix Herrmann-Westendorf, Thien H Ngo, Todd Martínez, Benjamin Dietzek, Jonathan P Hill, Katsuhiko Ariga, Mikalai M Kruk, Wouter Maes, Martin Presselt
Corroles are emerging as an important class of macrocycles with numerous applications because of their peculiar photophysical and metal chelating properties. meso-Pyrimidinylcorroles are easily deprotonated in certain solvents, which changes their absorption and emission spectra as well as their accessible supramolecular structures. To enable control over the formation of supramolecular structures, the dominant corrole species, i.e., the deprotonated form or one of the two NH-tautomers, needs to be identified...
November 16, 2017: Journal of Physical Chemistry. A
Kolanu Sudhakar, Amir Mizrahi, Monica Kosa, Natalia Fridman, Boris Tumanskii, Magal Saphier, Zeev Gross
Gold corroles are not readily accessible and they display no interesting physical or chemical properties. A facile methodology has now been developed for obtaining selectively CF3 -substituted gold(III) corroles and the introduction of these groups has been found to have an immense effect on the structures of the complexes, their photophysical and redox properties, and on their ability to participate in catalytic processes.
June 21, 2017: Angewandte Chemie
Abraham B Alemayehu, Nicholas U Day, Tomoyasu Mani, Alexander B Rudine, Kolle E Thomas, Odrun A Gederaas, Sergei A Vinogradov, Carl C Wamser, Abhik Ghosh
Two amphiphilic corroles-5,10,15-tris(3-carboxyphenyl)corrole (H3[mTCPC]) and 5,10,15-tris(4-carboxyphenyl)corrole (H3[pTCPC])-and their gold complexes have been synthesized, and their photophysical properties and photovoltaic behavior have been investigated. Like other nonpolar gold corroles, Au[mTCPC] and Au[pTCPC] were both found to exhibit room temperature phosphorescence in deoxygenated solutions with quantum yields of ∼0.3% and triplet lifetimes of ∼75 μs. Both compounds exhibited significant activity as dyes in photodynamic therapy experiments and in dye-sensitized solar cells...
July 27, 2016: ACS Applied Materials & Interfaces
Kostas Karikis, Evangelos Georgilis, Georgios Charalambidis, Athanasia Petrou, Olena Vakuliuk, Theodore Chatziioannou, Iliana Raptaki, Sofia Tsovola, Ioanna Papakyriacou, Anna Mitraki, Daniel T Gryko, Athanassios G Coutsolelos
A series of conjugates of amino acids with porphyrins and corroles was synthesized. Their self-assembling ability under defined conditions was investigated by scanning electron microscopy. The morphology and photophysical properties of these molecules were studied by absorption and fluorescence spectroscopy in solid, liquid, and self-assembled forms. We observed that both corrole and porphyrin conjugated with the l-phenylalanine-l-phenylalanine peptide to form spherical nanostructures with bathochromic shifts in the emission spectra, indicating the formation of aggregates...
August 1, 2016: Chemistry: a European Journal
Yogesh Kumar Maurya, Takahiro Ishikawa, Yasunori Kawabe, Masatoshi Ishida, Motoki Toganoh, Shigeki Mori, Yuhsuke Yasutake, Susumu Fukatsu, Hiroyuki Furuta
Novel near-infrared phosphorescent iridium(III) complexes based on benzo-annulated N-linked corrole analogue (termed as benzonorrole) were synthesized. The structures of the complexes revealed octahedral coordination geometries involving an organometallic iridium-carbon bond with two external axial ligands. Interestingly, the iridium(III) complex exhibits near-infrared phosphorescence at room temperature at wavelengths beyond 900 nm. The significant redshift of the emission, as compared to the corrole congener, is originated from the ligand-centered triplet character...
June 20, 2016: Inorganic Chemistry
Biju Basumatary, R V Ramana Reddy, Subhrajyoti Bhandary, Jeyaraman Sankar
Anchoring a BODIPY onto Ga(III)corrole via a meso-β linkage facilitated PeT in polar solvents, which quenched the fluorescence, and is further confirmed by electrochemical studies. The triad exhibits unprecedented crystal emission, which is not known for a corrole derivative, due to unique packing. Compound 4 hosts the first example of a novel B-F∙∙∙F interaction as well.
December 28, 2015: Dalton Transactions: An International Journal of Inorganic Chemistry
Christopher M Lemon, Daniel G Nocera
Whereas a variety of covalent conjugation strategies have been utilized to prepare quantum dot (QD)-based nanosensors, supramolecular approaches of self-assembly have been underexplored. A major advantage of self-assembly is the ability to circumvent laborious synthetic efforts attendant to covalent conjugation of a chemosensor to functionalized QDs. Here, we combine a CdSe/ZnS core-shell QD with gold(III) corroles using both self-assembly and micelle encapsulation to form QD nanosensors. Appreciable spectral overlap between QD emission and corrole absorption results in efficient Förster resonance energy transfer (FRET), which may be initiated by one- or two-photon excitation...
2015: Faraday Discussions
Bradley J Brennan, Yick Chong Lam, Paul M Kim, Xing Zhang, Gary W Brudvig
Organic dyes with their wide range of molecular structures and spectroscopic features show great promise for solar energy applications. Corroles, structural analogues to porphyrins, are highly fluorescent molecules with tunable properties. We have synthesized a series of structurally similar corroles chelating gallium and phosphorus, along with a β-chlorinated phosphorus corrole, and determined their photophysical and electrochemical properties. The electrochemical potentials to oxidize the corroles range from 0...
July 29, 2015: ACS Applied Materials & Interfaces
Biju Basumatary, Adiki Raja Sekhar, R V Ramana Reddy, Jeyaraman Sankar
A free-base and its Cu(III) derivative of bichromophoric meso-β linked corrole-BODIPY dyad were synthesized and structurally characterized by single crystal X-ray diffraction (XRD). Both corrole and BODIPY fragments maintained respective ground state electronic isolation despite their connection through a single bond due to a tilted orientation as observed by XRD. This was further supported by UV-vis and cyclic voltammetric studies. The Cu(III)-metalated dyad exhibits temperature-dependent paramagnetic behavior as observed in the variable temperature (1)H NMR due to the presence of a Cu(II)-corrole-π-cation radical...
May 4, 2015: Inorganic Chemistry
Lei Zhang, Zi-Yu Liu, Xuan Zhan, Li-Li Wang, Hui Wang, Hai-Yang Liu
The ultrafast photophysical behaviors of a series of meso-fluorophenyl substituted electron-deficient free base corroles F0C, F5C, F10C and F15C in toluene have been investigated using femtosecond time resolved absorption spectroscopy and steady-state spectroscopy. The S2→S1* transformation was found to be accelerated with the enhancement of electron-deficiency (from 550 fs for F0C to 140 fs for F15C), while S1*→S1 prolonged from ∼9 ps for F0C to ∼24 ps for F15C, which was assigned to an intermolecular vibrational cooling process...
May 2015: Photochemical & Photobiological Sciences
Christopher M Lemon, Robert L Halbach, Michael Huynh, Daniel G Nocera
Corroles are an emergent class of fluorophores that are finding an application and reaction chemistry to rival their porphyrin analogues. Despite a growing interest in the synthesis, reactivity, and functionalization of these macrocycles, their excited-state chemistry remains undeveloped. A systematic study of the photophysical properties of β-substituted corroles was performed on a series of free-base β-brominated derivatives as well as a β-linked corrole dimer. The singlet and triplet electronic states of these compounds were examined with steady-state and time-resolved spectroscopic methods, which are complemented with density functional theory (DFT) and time-dependent DFT calculations to gain insight into the nature of the electronic structure...
March 16, 2015: Inorganic Chemistry
Bin Liu, Hongyun Fang, Xiaofang Li, Wenting Cai, Lipiao Bao, Marc Rudolf, Fabian Plass, Louzhen Fan, Xing Lu, Dirk M Guldi
Embedding endohdedral metallofullerenes (EMFs) into electron donor-acceptor systems is still a challenging task owing to their limited quantities and their still largely unexplored chemical properties. In this study, we have performed a 1,3-dipolar cycloaddition reaction of a corrole-based precursor with Sc3 N@C80 to regioselectively form a [5,6]-adduct (1). The successful attachment of the corrole moiety was confirmed by mass spectrometry. In the electronic ground state, absorption spectra suggest sizeable electronic communications between the electron acceptor and the electron donor...
January 7, 2015: Chemistry: a European Journal
Jenya Vestfrid, Israel Goldberg, Zeev Gross
Facile procedures were developed for selective iodination of aluminum and gallium corroles; crystallographic characterization shows that the main structural aspects are not changed (the macrocycle remains planar). Absorption maxima are red-shifted by 3-5 nm/iodine, singlet lifetimes are reduced to <80 ps, and emissions from long-lived excited states come into effect. The iodinated corroles display prompt fluorescence, phosphorescence, and delayed thermal fluorescence, all at room temperature. The effect on redox potentials appears to be additive for each additional iodine and, surprisingly, is practically identical to that of the other three halides...
October 6, 2014: Inorganic Chemistry
Bertrand Brizet, Nicolas Desbois, Antoine Bonnot, Adam Langlois, Adrien Dubois, Jean-Michel Barbe, Claude P Gros, Christine Goze, Franck Denat, Pierre D Harvey
Red (no styryl), green (monostyryl), and blue (distyryl) BODIPY-gallium(III) (BODIPY = boron-dipyrromethene) corrole dyads have been prepared in high yields using click chemistry, and their photophysical properties are reported. An original and efficient control of the direction of the singlet energy transfers is reported, going either from BODIPY to the gallium-corrole units or from gallium-corroles to BODIPY, depending upon the nature of the substitution on BODIPY. In one case (green), both directions are possible...
April 7, 2014: Inorganic Chemistry
Georgios Rotas, Georgios Charalambidis, Lukas Glätzl, Daniel T Gryko, Axel Kahnt, Athanassios G Coutsolelos, Nikos Tagmatarchis
The preparation and characterization of the first corrole-azafullerene dyad are described. The photophysical and electrochemical properties of the new corrole-C59N dyad were examined and it was found that photoexcitation of the corrole unit leads to the formation of a charge separated state.
October 14, 2013: Chemical Communications: Chem Comm
Wenli Shao, Hui Wang, Shuang He, Lei Shi, Kaimei Peng, Yongfeng Lin, Lei Zhang, Liangnian Ji, Haiyang Liu
The luminescence, excited-state absorption, and singlet oxygen generation measurements were performed on three kinds of halogenated corroles: monohydroxyl halogenated corroles (Corrole-F, Corrole-Cl, Corrole-I), peripherally fluorine-substituted corroles (F0, F5, F10, F15), and gallium complexes (F10-Ga, F15-Ga). The fluorescence intensities progressively decrease whereas the triplet quantum yields, oxygen quenching rates, and singlet oxygen quantum yields increase with the increasing of the monohydroxyl halogen atomic weight...
December 13, 2012: Journal of Physical Chemistry. B
Elena Rabinovich, Israel Goldberg, Zeev Gross
Corrole complexes with gold(I) and gold(III) were synthesized and their structural, photophysical, and electrochemical properties investigated. This work includes the X-ray crystallography characterization of gold(I) and gold(III) complexes, both chelated by a corrole with fully brominated β-pyrrole carbon atoms. The mononuclear and chiral gold(I) corrole appears to be the first of its kind within the porphyrinoid family, while the most unique property of the gold(III) corrole is that it displays phosphorescence at ambient temperatures...
October 24, 2011: Chemistry: a European Journal
Joshua H Palmer, Alec C Durrell, Zeev Gross, Jay R Winkler, Harry B Gray
The photophysical properties of Ir(III) corroles differ from those of phosphorescent porphyrin complexes, cyclometalated and polyimine Ir(III) compounds, and other luminescent metallocorroles. Ir(III) corrole phosphorescence is observed at ambient temperature at wavelengths much longer (>800 nm) than those of most Ir(III) phosphors. The solvatochromic behavior of Ir(III)-corrole Soret and Q absorption bands suggests that the lowest singlet excited states (S(2) and S(1)) are substantially more polar than the ground state...
July 14, 2010: Journal of the American Chemical Society
Thien H Ngo, Fausto Puntoriero, Francesco Nastasi, Koen Robeyns, Luc Van Meervelt, Sebastiano Campagna, Wim Dehaen, Wouter Maes
meso-Pyrimidinyl-substituted AB(2)-corroles were efficiently synthesized starting from 5-mesityldipyrromethane and various 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. The corrole yield was significantly enhanced by optimization of the amount of Lewis acid catalyst (BF(3).OEt(2)). The main advantage of pyrimidinylcorroles over other meso-triarylcorroles is their wide range of functionalization possibilities, which has been explored by nucleophilic and electrophilic aromatic substitution, and Pd-catalyzed cross-coupling reactions...
May 17, 2010: Chemistry: a European Journal
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