Milen Bogdanov at Sofia Science Festival, 2013
First name / Surname: Milen Bogdanov
Faculty of Chemistry and Pharmacy,
University of Sofia “St Kliment Ohridski”,
1, James Bourchier blvd.,1164 Sofia,
Telephone: (+359 2) 81 61 228 (work)
Fax: (+359 2) 962 54 38 (work)
University of Sofia “St. Kl. Ohridski” / Faculty of Chemistry and Pharmacy / Department of Organic Chemistry
2011 – till now, Associate Professor in Organic Chemistry
2007 – 2011, Head Assistant Professor in Organic Chemistry
2005 – 2007, Senior Assistant Professor in Organic Chemistry
2001 – 2002 , Chemist at the Research Department.
Main activities and responsibilities: • Lecturer in “Organic Chemistry” (since 2009) • Lecturer in “Physical Organic Chemistry” (since 2007) • Lecturer in “Spectral Characterisation of Organic Compounds” (since 2011) • Lecturer in “How to Make Scientific Presentation” (since 2009) • Conductor of laboratory sessions and seminars in “Organic Chemistry” (since 2002) • Supervisor of PhD students • Supervisor of Ms and Bs students
Synthesis Pilot Plant, Chemical Pharmaceutical Research Institute, Sofia, Bulgaria
1996 – 2005, Technologist. Main activities and responsibilities: • Large scale synthesis of bioactive substances
2002 – 2005, Graduated in 2005 as Philosophy Doctor (PhD) from University of Sofia “St. Kl. Ohridski”
Title of Thesis: Synthesis and conformational analysis of diastereomeric isochromanones and tetrahydroisoquinolinones. Supervisor: Prof. Dr. Mariana Palamareva, D.Sc. Principal subjects/occupational skills covered: • Synthesis and spectral characterization of heterocyclic compounds • Multi-step synthesis • Separation of complex reaction mixtures • Isolation, purification and characterisation of unknown organic compounds • Conformational analysis
1996 – 2001, Graduated in 2001 as Master of Science from University of Sofia “St. Kl. Ohridski”. Master’s program: Organic and analytical chemistry. Title of Diploma Thesis: Synthesis of 4-[(N,N-disubstituted)-aminomethyl]-2-phenethil-3-thienil-1,2,3,4-tetrahydroisoquinoline-1-ones. Supervisor: Prof. Dr. Mariana Palamareva, D.Sc.
1989 – 1994, Graduated in 1994 as Chemical technologist from High School with Enhanced Chemistry Training, Sofia
12 – 16 of June 2007, Second Residential Summer School for Newly Appointed University Chemistry Teaching Staff, Sliema, Malta.
01 – 10 of July 2006, Summer School for Newly Appointed University Teaching Staff, Kiten, Bulgaria.
University of Applied Sciences, Aalen, Germany – 12.2007-09.2008 (10 months); 02.2009-09.2009 (8 months)
Postdoc position in the group of Prof. Dr. W. Kantlehner. Principal subjects covered: Synthesis, characterisation, measurements of physico-chemical properties and application of guanidinium-based Ionic liquids
Drug design • Organic synthesis • Heterocyclic compounds • Ionic Liquids • Stereochemistry • Chromatography • Spectral methods • Conformational analysis
Professional and Scientific Awards
• Second place in FameLab-Bulgaria, 2011 • Best young scientist of University of Sofia “St. Kl. Ohridski” for 2010 • Medal of honor of Faculty of Chemistry, University of Sofia “St. Kl. Ohridski” for 2010• Nomination for Pythagoras Award, category “Best young scientist of Bulgaria” for 2009
Membership in scientific organizations
• International Union of Pure and Applied Chemistry (IUPAC) • European Chemistry Thematic Network (ECTN) • Union of Chemists in Bulgaria • European Association for Chemical and Molecular Sciences • Federation of Scientific and Technical Unions
Personal skills and competences
Organisational skills and competences: • Leader of a Research group • Manager of the Career centre at the Faculty of Chemistry and Pharmacy • Founder and Editor-in-Chief of scientific journal “Bulgarian Journal of Chemistry” • Project Leader of 4 scientific projects • Member of the organization committee of international conferences ImSaT-9 and SizeMat-2 • Supervisor of 12 MS diploma theses • Supervisor of 4 PhD students • Supervisor of undergraduate students
Computer skills and competences: Competent at high level with: • Win XP/7 • Microsoft Office tools (Word, Excel and PowerPoint) • ChemOffice program package (ChemDraw, Chem3D, ChemFinder) • Crystallographic software (Wingx, Ortep, Mercury, enCIFer) • NMR spectroscopy software (MestRe-C, TopSpin) • Chromatography software (LSChrom) • Design (Adobe Photoshop, Neat image, Panorama factory, Scribus)
Outdoor activities and hobbies: mountaineering • biking • photography
Sep. Purif. Technol. 103 (2013) 279-288 Ionic liquid-supported solid–liquid extraction of bioactive alkaloids. II. Kinetics, modeling and mechanism of glaucine extraction from Glaucium flavum Cr. (Papaveraceae)
The temperature dependence on the global kinetics of both methanol and 1-butyl-3-methylimidazolium acesulfamate ([C4mim][Ace])-supported extraction of the bioactive alkaloid S-(+)-glaucine from plant material of Glaucium flavum Crantz (Papaveraceae) was measured and a comparative analysis in respect to the extractant type was performed. The experimental data was fitted with high coefficients of determination by means of an empirical model showing that the extraction process in both cases follows second-order kinetics. The concentration at saturation, Cs, extraction rate constants, k2, initial rates of extraction, h, and activation energies of extraction, Ea, were then calculated and discussed. The obtained results give a considerable advantage to the Ionic liquid-supported (IL-supported) extraction procedure due to the faster and quantitative glaucine transfer, regardless the temperature. A plausible extraction mechanism scenario, describing the whole system in terms of solute–solvent, solute–matrix and matrix–solvent interactions at every stage of the extraction process was proposed. As a result, the apparent kinetics and yield of the IL-supported extraction were attributed to the cell wall modification by H-bonding interactions between both ions of [C4mim][Ace] and cellulose, resulting in the plant tissues disruption. The latter was further unequivocally confirmed by means of scanning electron microscopy. The kinetics parameters obtained were then implemented into a model for the prediction of glaucine amount extracted in 1 M [C4mim][Ace] water solution at any temperature and time with good predictive ability.
Sep. Purif. Technol. 97 (2012) 221-227 Ionic liquid-supported solid–liquid extraction of bioactive alkaloids. I. New HPLC method for quantitative determination of glaucine in Glaucium flavum Cr. (Papaveraceae)
A series of hydrophilic 1-alkyl-3-methylimidazolium-based ionic liquids were used as extractants for the effective extraction of S-(+)-glaucine from plant material of Glaucium flavum Crantz (Papaveraceae). The extractions were carried out both under ultrasonic and conventional heating conditions and the extraction efficiency was monitored by HPLC. The influence of the anion (chloride, bromide, acesulfamate and saccharinate), alkyl chain length in the imidazolium ion, concentration, extraction time, and plant material/extractant ratio was investigated. A comparative study between conventional Soxhlet extraction with methanol as a solvent (total extraction) and water solutions of ILs shows the same extraction ability of ILs, but with significantly reduced extraction time. Moreover, the extraction efficiency was shown to be strongly anion dependent. The results obtained provide a fast and safe method for determination of glaucine in G. flavum Cr.
Eur. J. Org. Chem. (2011) 377 - 384 New Perkin/Michael/Addition Domino Reaction Between Homophthalic Anhydride and Aromatic Aldehydes: A Facile Approach to Blue Fluorescent 6-oxo-dibenzo[c,h]chromenes
A series of new trans-11-aryl-6-oxo-6H-dibenzo[c,h]chromene-12-carboxylic acids has been synthesised through anew Perkin/Michael addition domino reaction between homophthalic anhydride and aromatic aldehydes. The synthesis is straightforward and gives good overall yields by taking into account the concomitant formation of four C–C, C–O and C=C bonds. The structures of the newly synthesised compounds were established by spectroscopic methods (1H NMR, 13C NMR and IR) and X-ray diffraction analysis, and the fluorescent properties were investigated. A probable reaction mechanism including three proven intermediates is proposed.
Z. Naturforsch. 65b (2010) 37 – 48 New Guanidinium Based Room Temperature Ionic Liquids. Substituent and Anion Effect on Density, Polarity and Solubility in Water
In order to examine the influence of the alkyl chain length on some physical properties of guanidiniumsalts, the synthesis of a homologous series of new N-n-alkylsubstituted N,N-diethyl-N,N-di-n-propyl-N-n-hexyl guanidinium ionic liquids (gILs), containing chloride (Cl), tetrafluoroborate(BF4), acesulfamate (Ace), saccharinate (Sac), and tosylate (Tos) as anions, is reported. Cn-gILAce,Cn-gILSac, and Cn-gILBF4 were obtained by ion exchange reaction of the corresponding hexasubstitutedguanidinium chlorides (Cn-gCl, n = 3, 4, 6, 8, 10), which were synthesized by a quaternizationreaction of the pentaalkyl-substituted guanidine 3 and the corresponding alkylchloride in DMF.The tosylates gILs Cn-gTos (n = 1, 2, 4, 6, 8, 10) were synthesized by alkylation of 3 with the correspondingalkyltosylates. Some physical properties, such as solubility in water and organic solvents,refractive index and density, are considered as a function of the length of the n-alkyl substituent Rand the nature of the anion.
Z. Naturforsch. 64b (2009) 756 – 764 Residual Volume Approach II. Simple Prediction of Ionic Conductivity of Ionic LiquidsDescription
The Residual Volume Approach (RVA), a recently developed method for the prediction of fundamentalphysical properties of ionic liquids (ILs) is extended and now allows the estimation of ionicconductivity of unknown ILs, using a simple linear correlation between the ionic conductivity andpreviously defined substituent parameters – β X. The proposed method is applied to the conductivitycorrelations of 61 n-alkyl substituted imidazolium, tetraalkylammonium, pyrrolidinium, piperidinium,sulfonium and phosphonium homologous ILs, containing [BF4]−, [Tf2N]−, [C2 F5PF]−,[CF3BF3]−, [C2H5BF3]−, [F(HF)2.3]−, [Br]−, [I]−, and [formate]− as anions. The influence of theion type – both anion and cation – on the property changes is discussed. Moreover, it is shown thatrelatively rigid cations with C2 symmetry decrease the expected conductivity in the same manner as they increase the viscosity of the ILs.