Karl M. Kadish

University of Houston, Houston, Texas, United States

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Publications (608)2766.68 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Herein we report the syntheses and comparative photophysical, electrochemical, in vitro, and in vivo biological efficacy of 3-(1'-hexyloxy)ethyl-3-devinylpyropheophorbide-cyanine dye (HPPH-CD) and the corresponding indium (In), gallium (Ga), and palladium (Pd) conjugates. The insertion of a heavy metal in the HPPH moiety makes a significant difference in FRET (Förester resonance energy transfer) and electrochemical properties, which correlates with singlet oxygen production [a key cytotoxic agent for photodynamic therapy (PDT)] and long-term in vivo PDT efficacy. Among the metallated analogs, the In(III) HPPH-CD showed the best cancer imaging and PDT efficacy. Interestingly, in contrast to free base HPPH-CD, which requires a significantly higher therapeutic dose (2.5 mol/kg) than imaging dose (0.3 mol/kg), the corresponding In(III) HPPH-CD showed excellent imaging and therapeutic potential at a remarkably low dose (0.3 mol/kg) in BALB/c mice bearing Colon26 tumors. A comparative study of metallated and corresponding non-metallated conjugates further confirmed that STAT-3 dimerization can be used as a biomarker for determining the level of photoreaction and tumor response.
    No preview · Article · Jan 2016 · Bioconjugate Chemistry
  • Nitika Grover · Muniappan Sankar · Yang Song · Karl M Kadish
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    ABSTRACT: A new series of β-substituted octaphenylporphyrins were synthesized and the influence of unsymmetrical substitution on the photophysical and electrochemical properties of the compounds is elucidated. The examined compounds are represented as MOPP(R)X2 where OPP = the dianion of octaphenylporphyrin, R = NO2, CHO, or CH2OH, X = Br or CN, and M is Co(II), Cu(II), Ni(II), or Zn(II). Routes to the trifunctionalized β-octaphenylporphyrins begin with the synthesis of MOPP(R) (R = NO2, CHO, and CH2OH) and the conversion of MOPP(NO2) to MOPP(NO2)X2 (X = Br and CN). These "push-pull" octaphenylporphyrins exhibit high dipole moments, tunable redox properties, and red-shifted electronic spectral features due to asymmetric β-substitution. Photophysical data on the series of MOPP(R)X2 compounds also reflect the nonplanar conformation of these porphyrins. Quantum yield and lifetime data are invariably lower than what has been reported in the literature for related β-substituted porphyrins. The spectroscopic properties and electrochemical redox potentials of the porphyrins are influenced by both the peripheral substituents and nature of the core metal ion. A decrease in the HOMO-LUMO gap and increase in Δb1 is observed as the number of electron withdrawing groups on the molecule was increased. In addition, a tuning of the redox potentials could be achieved by introducing both electron donating (CH2OH) and withdrawing (CN, NO2, CHO, and Br) substituents into the MOPP skeleton which led to a "cross-polarized push-pull effect" of the β-substituents and a nonplanarity of the molecule. Metal-centered oxidations were exhibited for all of the Co(II) porphyrins and an M(II)/M(III) process was also observed to occur for NiOPP(R) (R = CH2OH, H, CHO, and NO2) and CuOPP(NO2)(CN)2. These electrode reactions for the latter two series of compounds occur after an initial conversion of the neutral porphyrin to its dicationic form under the electrochemical conditions. Evidence for the site of electron transfer is given in part by comparison with data in the literature for related compounds and in part by theoretical calculations and thin-layer spectroelectrochemical data carried out in the current study.
    No preview · Article · Dec 2015 · Inorganic Chemistry
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    ABSTRACT: Metalation of 6,13,20,21-tetrakis-aryl-22H-[14]tribenzotriphyrin(2.1.1) (TriPs) with PdCl2 provides Pd(II)-TriP complexes in 45-56% yields. The complexes were characterized by mass spectrometry, and UV-visible absorption, magnetic circular dichroism, and (1)H NMR spectroscopy. A single crystal X-ray analysis reveals that the Pd(II)-TriPs adopts a deeply saddled conformation. The palladium(II) ion is coordinated by two pyrrole nitrogen atoms and two chloride ions to form the square-planar coordination environment. The redox properties of the Pd(II)-TriPs were studied by cyclic voltammetry. Each compound undergoes one irreversible and two reversible one-electron reductions. There is a marked red-shift of the main spectral bands, relative to those of the free-base TriP ligand, due to a marked relative stabilization of the LUMO upon coordination by PdCl2.
    No preview · Article · Nov 2015 · Inorganic Chemistry
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    ABSTRACT: The synthesis of a series of beta-functionalized push-pull dibenzoporphyrins was realized. These porphyrins display subtle push-pull effects, demonstrating the exceptional tunability of their electronic and electrochemical properties. The UV-Vis spectra of these porphyrins show unique absorption patterns and the fluorescence spectra of these porphyrins display strong near-IR emission bands. In particular, fluorescence quenching effect was observed for pyridyl carrying push-pull porphyrin 4c in the presence of an acid. The versatile synthetic methods developed in this work may open a door to access a large number of functionalized organic materials that are currently unavailable. The structure-property studies provided in this work may provide useful guidelines for the design of new generations of materials in dye-sensitized solar cells, in non-linear optical applications, as fluorescence probes, as well as sensitizers for photodynamic therapy.
    No preview · Article · Nov 2015 · The Journal of Organic Chemistry

  • No preview · Article · Nov 2015 · Chemistry - A European Journal
  • Ru Feng · Zhongping Ou · zhaoli Xue · Yuanyuan Fang · Yang Song · Karl M. Kadish
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    ABSTRACT: Three meso-substituted pyrrole-terminated tripyrrins were isolated for the first time as side products in the synthesis of triarylcorroles and characterized by spectroscopic and electrochemical techniques. The examined compounds are represented as (Ar)2TriPyH, where the TriPy is the conjugated tripyrrin monoanion and Ar a 2,6-diFPh, 2,6-diClPh or 2,4-diClPh substituent. A single crystal X-ray structure of (2,6-diFPh)2TriPyH is also presented. This is the first X-ray structure of a meso-aryl substituted tripyrrin. Each tripyrrin undergoes two reductions and three oxidations in CH2Cl2. The first one-electron addition and first one-electron abstraction lead to formation of π-anion and π-cation radicals with a potential separation between the two processes of 1.71 to 1.76 V. However, both electrogenerated products are unstable and undergo a rapid chemical reaction to give new electroactive species which are identified as the deprotonated and protonated compounds, respectively. The reaction products were characterized by spectroelectrochemistry and comparisons are made with spectroscopic data obtained during base and acid titrations in CH2Cl2.
    No preview · Article · Nov 2015 · RSC Advances
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    ABSTRACT: A detailed study of reduction potentials, electroreduction mechanisms, and acid-base chemistry was carried out on two series of free-base porphyrins in nonaqueous media. The first series is represented by four β-pyrrole-substituted tetraphenylporphyrin (TPP) derivatives, two of which are planar and two of which are nonplanar in their nonprotonated form. The second comprises porphyrins with 0-4 meso-phenyl groups on the macrocycle. Equilibrium constants for the conversion of each neutral porphyrin to its diprotic [H4P]2+ form were determined and the electrochemistry was then elucidated as a function of: 1)type of nonaqueous solvent, 2)anion of supporting electrolyte, 3)porphyrin ring substituents, and 4)concentration of acid added to solution. Spectroelectrochemistry was used to characterize absorption spectra of each electroreduced species and, when combined with results of the above studies, significantly improves our ability to tune redox reactivity of these types of compounds.
    No preview · Article · Nov 2015
  • Guifen Lu · Jing Li · Sen Yan · Cheng He · Mengying Shi · Weihua Zhu · Zhongping Ou · Karl M. Kadish
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    ABSTRACT: Two heteroleptic corrole–phthalocyanine europium triple-decker complexes were fabricated into organic nanostructures by the standard phase-transfer method. The investigated compounds are represented by Eu2(Pc)2[Cor(ClPh)3] (1) and Eu2[Pc(OC8H17)8]2[Cor(ClPh)3] (2), where Pc represents the dianion of phthalocyanine and Cor(ClPh)3 the trianion of 5,10,15-tri(4-chlorophenyl)corrole. Both compounds 1 and 2 show typical electronic absorption spectra for a non-aggregated molecular structure in chloroform or toluene. However, in methanol compound 1 self-assembled into belt-like nanostructures while compound 2, which possesses long OC8H17 alkoxy side chains, self-assembled into large scale sheet-like nanostructures. The third-order nonlinear optical properties of both triple-decker compounds were also investigated in toluene by the Z-scan technique and characterized as showing nonlinear reverse saturation absorption and self-defocusing behavior. A third-order nonlinear optical susceptibility, χ(3), of 3.18 × 10−10 and 3.35 × 10−10 esu was obtained for 1 and 2, respectively, thus indicating the potential application of these compounds in the field of optical devices.
    No preview · Article · Oct 2015 · Dyes and Pigments
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    ABSTRACT: Complexes of 5,10,15-triferrocenylcorrole were synthesized from the crude free-base corrole product obtained by the reaction of ferrocenyl aldehyde and pyrrole. Direct formation of the complex in this manner leads to an increase of the reaction yield by protecting the corrole ring toward oxidative decomposition. The procedure was successful and gave the expected product in the case of the copper and triphenylphosphinecobalt complexes, but an unexpected result was obtained in the case of the nickel derivative, where metal insertion led to a ring opening of the macrocycle at the 5 position, giving as a final product a linear tetrapyrrole nickel complex bearing two ferrocenyl groups. The purified 5,10,15-triferrocenylcorrole complexes have been fully characterized by a combination of spectroscopic methods, electrochemistry, spectroelectrochemistry, and density functional theory calculations. Copper derivatives of 10-monoferrocenyl- and 5,15-diferrocenylcorrole were prepared to investigate how the number and position of the ferrocenyl groups influenced the spectroscopic and electrochemical properties of the resulting complexes. A complete assignment of resonances in the (1)H and (13)C NMR spectra was performed for the cobalt and nickel complexes, and detailed electrochemical characterization was carried out to provide additional insight into the degree of communication between the meso-ferrocenyl groups on the conjugated macrocycle and the central metal ion of the ferrocenylcorrole derivatives.
    No preview · Article · Oct 2015 · Inorganic Chemistry
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    ABSTRACT: Twelve structurally related pyridyl and meso-N-methylpyridylporphyrin derivatives are investigated by electrochemistry in different non-aqueous media. The UV/Vis spectrum of each newly investigated porphyrin was measured before and after electroreduction and, based on this data, the site of electron transfer is proposed. An interaction occurs between the meso-pyridyl or meso-N-alkyl-4-pyridyl substituents and the porphyrin π-ring system, the magnitude of which depends upon the number of linked pyridyl or N-alkyl-4-pyridyl groups on the compound, the solvent, the supporting electrolyte and/or other anions added to solution.
    No preview · Article · Oct 2015
  • Guifen Lu · Jing Li · Xiaoqin Jiang · Zhongping Ou · Karl M Kadish
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    ABSTRACT: A series of europium triple-decker complexes containing phthalocyanine and nitrophenyl-corrole macrocycles were synthesized and characterized by spectroscopic and electrochemical methods in nonaqueous media. The examined compounds are represented as Eu2[Pc(OC4H9)8]2[Cor(Ph)n(NO2Ph)3-n], where n varies from 0 to 3, Pc(OC4H9)8 represents the phthalocyanine macrocycle, and Cor indicates the corrole macrocycle having phenyl (Ph) or nitrophenyl (NO2Ph) meso substituents. Three different methods were used for syntheses of the target complexes, two of which are reported here for the first time. Each examined compound undergoes five reversible one-electron oxidations and 3-5 one-electron reductions depending upon the number of NO2Ph substituents. The nitrophenyl groups on the meso positions of the corrole are highly electron-withdrawing, and this leads to a substantial positive shift in potential for the five oxidations and first reduction in CH2Cl2, PhCN, or pyridine as compared to the parent triple-decker compound with a triphenylcorrole macrocycle. The measured E1/2 values are linearly related to the number of NO2Ph groups on the corrole, and the relative magnitude of the shift in potential for each redox reaction was used in conjunction with the results from thin-layer spectro-electrochemistry to assign the initial site of oxidation or reduction on the molecule. The nitrophenyl substituents are also redox-active, and each is reduced to [C6H4NO2](-) in a separate one-electron transfer step at potentials between -1.12 and -1.42 V versus saturated calomel electrode.
    No preview · Article · Sep 2015 · Inorganic Chemistry
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    ABSTRACT: A silver β-octabromo-meso-triarylcorrole has been found to exhibit a strongly saddled geometry, providing the first instance of a strongly saddled corrole complex involving a metal other than copper. The Soret maxima of the Ag octabromocorroles also redshift markedly in response to increasingly electron-donating para substituents on the meso-aryl groups. In both these respects, the Ag octabromocorroles differ from simple Ag triarylcorrole derivatives, which exhibit only mild saddling and substituent-insensitive Soret maxima. These results have been rationalized in terms of an innocent M(III) -corrole(3-) description for the simple Ag corroles and a noninnocent M(II) -corrole(.2-) description for the Ag octabromocorroles. In contrast, all copper corroles are thought to be noninnocent, while all gold corroles are innocent. Uniquely among metallocorroles, silver corroles thus seem poised on a knife-edge, so to speak, between innocent and noninnocent electronic structures and may tip either way, depending on the exact nature of the corrole ligand.
    No preview · Article · Sep 2015 · Chemistry - A European Journal
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    ABSTRACT: Two series of copper tetraarylporphyrins containing β,β′-fused tetrabutano or tetrabenzo groups were synthesized and characterized as to their electrochemistry and spectroelectrochemistry in nonaqueous media. The examined compounds are represented as butano-(TpYPP)CuII and benzo-(TpYPP)CuII, where TpYPP is the porphyrin dianion and Y is a CH3, H or Cl substituent on the para-position of the four meso-phenyl rings of the compound. Each neutral porphyrin in the two series is ESR active and shows a typical d9 Cu(ii) signal in frozen CH2Cl2 solution. Each Cu(ii) porphyrin also undergoes two reversible one-electron reductions and two reversible one-electron oxidations in DMF or CH2Cl2 containing 0.1 M tetra-n-butylammonium perchlorate to give a π-anion radical and dianion upon reduction and a π-cation radical and dication upon oxidation. A third one-electron oxidation is also observed for butano-(TpYPP)Cu (Y = CH3 and H) and benzo-(TPP)Cu in PhCN and this process is assigned to the CuII/CuIII transition. The reversible half-wave potential for the first oxidation of each compound in both series is shifted negatively by about 500 mV as compared to E1/2 values for oxidation of the related copper tetraarylporphyrin without the four fused benzo or butano rings while smaller positive shifts of 60 and 300 mV are seen for reduction of the tetrabenzotetraarylporphyrins and tetrabutaotetraarylporphyrins, respectively, as compared to the same redox reactions of the related tetraarylporphyrins. The electrochemically measured HOMO-LUMO gap averages 1.76 ± 0.05 V for benzo-(TpYPP)CuII, 2.04 ± 0.06 V for butano-(TpYPP)CuII and 2.33 ± 0.03 for (TpYPP)Cu in CH2Cl2. This journal is
    No preview · Article · Sep 2015 · RSC Advances
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    ABSTRACT: Four nitrated N-confused free-base tetraarylporphyrins were synthesized and characterized by electrochemistry and spectroelectrochemistry in nonaqueous media. The examined compounds are represented as NO2(Ar)4NcpH2, where NO2(Ar)4Ncp is the dianion of a tetraaryl N-confused porphyrin with an inner carbon bound NO2 group and Ar is a p-CH3OPh, p-CH3Ph, Ph or p-ClPh substituent on each meso-position of the macrocycle. UV/Vis spectra and NMR spectroscopy data indicate that the same form of the porphyrin exists in CH2Cl2 and DMF which is unlike the case of non-NO2 N-confused porphyrins. The Soret band of NO2(Ar)4NcpH2 exhibits a 30–36 nm red-shift in CH2Cl2 and DMF as compared to the spectrum of the non-NO2 N-confused porphyrins. The first two reductions and first oxidation of NO2(Ar)4NcpH2 are reversible in CH2Cl2 containing 0.1 M TBAP. The measured HOMO–LUMO gap averages 1.65 V in CH2Cl2 and 1.53 V in DMF, with both values being similar to those of the non-NO2 substituted compounds. The nitro group on the inverted pyrrole is itself not reduced within the negative potential limit of CH2Cl2 or DMF, but its presence significantly affects both the UV/Vis spectra and redox potentials.
    No preview · Article · Aug 2015 · Chemistry - A European Journal
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    ABSTRACT: The synthesis and physicochemical characterization of a new class of water soluble homo/heteropentanuclear porphyrazine complexes are described. The investigated compounds, prepared from the previously reported mononuclear species [LM].xH2O (L = tetrakis-2,3-[5,6-di(2-pyridyl) pyrazino]porphyrazinato dianion; M = MgII(H2O), ZnII, CuII, CoII, PdII, PtII;x =3-8) in DMSO under mild experimental conditions, are represented as [{Pd(OAc)2}4LM].xH2O (x=11-22) and bear four Pd(OAc)2 units, each externally coordinated at the vicinal pyridine N atoms of a single dipyridinopyrazine fragment of the porphyrazine macrocycle ("py-py" coordination). The newly synthesized compounds were examined by IR and magnetic susceptibility measurements in the solid state. Solution UV-visible spectral studies on all of the species were conducted in the low-donor organic solvents pyridine, dimethyl sulfoxide and dimethylformamide and in the water medium, whereas electrochemical measurements were performed in these media in the presence of tetrabutylammonium perchlorate (organic solvents) and KCl or NaOAc (water). Data on the photosensitizing activity for the generation of singlet oxygen, 1O2, of interest in photodynamic therapy, were also obtained in dimethylformammide solution on the compounds [{Pd(OAc)2}4LM] (M = MgII(H2O), ZnII, PdII, PtII) and the measured φΔ values are presented and discussed. NMR spectral data on the complex [{Pd(OAc)2}4LZn] are also included and discussed.
    No preview · Article · Aug 2015 · Journal of Porphyrins and Phthalocyanines
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    ABSTRACT: Two-photon absorption and electrochemical properties of carbazole-linked porphyrin tweezers including a bisporphyrin dimer resulting from a Glaser homocoupling have been prepared and fully characterized by C. P. Gros, F. Bolze, K. M. Kadish, and co-workers. The dyads reported present a two-photon absorption maximum at 920 nm with two-photon absorption cross-section in the 1200 GM range. The comprehensive report can be found in the Full Paper on page 12018 ff.
    Preview · Article · Aug 2015 · Chemistry - A European Journal
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    ABSTRACT: Herein the synthesis, spectroscopic characterization, two-photon absorption and electrochemical properties of 3,6-disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl-carbazole spacer and a 5-bromo-triarylporphyrin and the properties of this original compound were compared with the 3,6-disubstituted carbazole bisporphyrin tweezers. The dyads reported herein present a two-photon absorption maximum at 920 nm with two-photon absorption cross-section in the 1200 GM range. Despite a strong linear absorption in the Soret region and moderate fluorescence quantum yield, they both lead to a high brightness reaching 30 000 M(-1) cm(-1) . © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    No preview · Article · Jul 2015 · Chemistry - A European Journal
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    ABSTRACT: The synthesis of unsymmetrical push-pull benzoporphyrins has been realized. UV-Vis and fluorescence spectroscopy, cyclic voltammetry and DFT calculations reveal subtle substituent effects on the electronic and optical properties of these porphyrins.
    No preview · Article · Jun 2015 · RSC Advances
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    ABSTRACT: Three meso-tetraaryl substituted N-5 sapphyrins were synthesized by a facile synthetic route from the corresponding open-chain pentapyrroles in high yield using acetic acid as the solvent and catalyst. Each compound was characterized by spectroscopic and electrochemical methods and the inverted pyrrole structure was confirmed in the solid state for the first time by single crystal X-ray analysis.
    No preview · Article · Jun 2015 · Journal of Porphyrins and Phthalocyanines
  • Guifen Lu · Jing Li · Sen Yan · Weihua Zhu · Zhongping Ou · Karl M Kadish
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    ABSTRACT: We recently reported the first example of a europium triple-decker tetrapyrrole with mixed corrole and phthalocyanine macrocycles and have now extended the synthetic method to prepare a series of rare earth corrole-phthalocyanine heteroleptic triple-decker complexes, which are characterized by spectroscopic and electrochemical methods. The examined complexes are represented as M2[Pc(OC4H9)8]2[Cor(ClPh)3], where Pc = phthalocyanine, Cor = corrole, and M is Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), or Tb(III). The Y(III) derivative with OC4H9 Pc substituents was obtained in too low a yield to characterize, but for the purpose of comparison, Y2[Pc(OC5H11)8]2[Cor(ClPh)3] was synthesized and characterized in a similar manner. The molecular structure of Eu2[Pc(OC4H9)8]2[Cor(ClPh)3] was determined by single-crystal X-ray diffraction and showed the corrole to be the central macrocycle of the triple-decker unit with a phthalocyanine on each end. Each triple-decker complex undergoes up to eight reversible or quasireversible one-electron oxidations and reductions with E1/2 values being linearly related to the ionic radius of the central ions. The energy (E) of the main Q-band is also linearly related to the radius of the metal. Comparisons are made between the physicochemical properties of the newly synthesized mixed corrole-phthalocyanine complexes and previously characterized double- and triple-decker derivatives with phthalocyanine and/or porphyrin macrocycles.
    No preview · Article · May 2015 · Inorganic Chemistry

Publication Stats

15k Citations
2,766.68 Total Impact Points

Institutions

  • 1979-2015
    • University of Houston
      • Department of Chemistry
      Houston, Texas, United States
  • 2010
    • Osaka University
      • Department of Materials Engineering Science
      Suika, Ōsaka, Japan
  • 2003-2007
    • University of Texas at Austin
      • • Department of Chemistry and Biochemistry
      • • Institute for Cellular and Molecular Biology
      Austin, Texas, United States
    • Houston Baptist University
      Houston, Texas, United States
    • Sapienza University of Rome
      • Department of Chemistry
      Roma, Latium, Italy
  • 2006
    • Louisiana State University Health Sciences Center New Orleans
      New Orleans, Louisiana, United States
  • 2004-2006
    • University of Tsukuba
      • Graduate School of Pure and Applied Sciences
      Tsukuba, Ibaraki, Japan
  • 2005
    • University of Sydney
      • School of Chemistry
      Sydney, New South Wales, Australia
  • 1994-2005
    • University of Cologne
      • Institute of Organic Chemistry
      Köln, North Rhine-Westphalia, Germany
  • 2003-2004
    • French National Centre for Scientific Research
      Lutetia Parisorum, Île-de-France, France
  • 1993-2004
    • University of Burgundy
      • Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB)
      Dijon, Bourgogne, France
  • 2001
    • Roswell Park Cancer Institute
      Buffalo, New York, United States
  • 1993-1999
    • University of California, Davis
      • Department of Chemistry
      Davis, California, United States
    • University of Rome Tor Vergata
      Roma, Latium, Italy
  • 1996-1998
    • Wichita State University
      • Department of Chemistry
      Wichita, Kansas, United States
  • 1989
    • Centre Hospitalier Universitaire de Dijon
      Dijon, Bourgogne, France
  • 1988
    • Mohammed V University of Rabat
      Rabat, Rabat-Salé-Zemmour-Zaër, Morocco
    • Princeton University
      • Department of Chemical and Biological Engineering
      Princeton, New Jersey, United States
  • 1980-1982
    • Houston Zoo
      Houston, Texas, United States
    • Rice University
      Houston, Texas, United States
  • 1973-1977
    • California State University, Fullerton
      • Department of Chemistry & Biochemistry
      Fullerton, California, United States
  • 1972
    • Louisiana State University
      • Department of Chemistry
      Baton Rouge, Louisiana, United States