An IV 2014

Third stage report

Previously obtained result we have organized in order to be published in two scientific papers.

Stage I. Synthesis and structural analysis of new N1-alkylated imidazole derivatives:

These results were published in: Ghe. Zbancioc, I. Mangalagiu, C. Moldoveanu: Ultrasound assisted synthesis of imidazolium salts: an efficient way to ionic liquids; Ultrasonics Sonochem, 23(c), 376-384, 2015. DOI: 10.1016/j.ultsonch.2014.10.028.

Stage II. Synthesis and structural analysis of imidazolium salts, and of pyrroloimidazole cycloadducts. Testing the properties, structural analysis and theoretical study of fluorescence for the synthesized compounds:

II.1. Synthesis of imidazolium salts by quaternization of the N3 of imidazole derivatives (obtained in stage I.1. or I.2.) using conventional heating.

These results were published in: Ghe. Zbancioc, I. Mangalagiu, C. Moldoveanu: Ultrasound assisted synthesis of imidazolium salts: an efficient way to ionic liquids; Ultrasonics Sonochem, 23(c), 376-384, 2015. DOI: 10.1016/j.ultsonch.2014.10.028.

II.2., II.3., II.4., II.5. si II.6. Synthesis of cycloadducts derived from imidazolium salts (obtained in stage II.1.) by [3+2] dipolar cycloaddition with activated alkynes and alkenes symmetrically and unsymmetrical substituted by conventional heating and under ultrasound irradiation.

These results were organized in an article submited to publication: C. Moldoveanu, Ghe. Zbancioc, D. Mantu, D. Maftei, I. Mangalagiu: The cycloaddition of the benzimidazolium ylides with alkynes: new mechanistic insights; Tetrahedron Letters, 56, xxx-xxx, 2015. (under review).

Stage III. Synthesis and structural analysis of new imidazolium hexafluorophosphates, as potential ionic liquids, and of new bis-imidazole derivatives. Testing the properties and structural analysis for the synthesized compounds:

III.1. Synthesis of new imidazolium hexafluorophosfaes from corresponding halides (obtained in stage II.1.) by anion metathesis.

We have improved this method by using ultrasound irradiation as an alternative way for the homogenization of the reaction mixture.

Stage IV. Synthesis of N-Heterocyclic Carbene Complexes derived from imidazole. Testing the properties and structural analysis for the synthesized compounds.

IV.1. IV.2. Synthesis of new macrocyclic structures

New macrocyclic structures with imidazol skeleton were obtained by the reaction of bis-imidazole derivatives with aliphatic (previously obtained in stage III.4.) or aromatic (previously obtained in stage III.5.) spacer with dihalogenoderivatives with enhanced reactivity such as diiodoalkanes.

IV.3. IV.4. Synthesis of crown carbene complexes

Crown carbene complexes were obtained by the reaction of cyclic imidazolium salts ((H4)4+(I–)4 obtained in stage IV.1. and IV.2.) with palladium iodide in DMSO in the presence of sodium acetate.

Also crown carbene complexes were obtained by the reaction of cyclic imidazolium salts ((H4)4+(I–)4 obtained in stage IV.1. and IV.2.) with copper oxide in DMSO in the presence of sodium acetate.

The structure of the new compounds was or will be chemical (elemental analysis) and spectral determined (IR, UV-VIS, NMR, MS).

The structure of the compounds was proved for all imidazole derivatives by elemental analysis and spectral analyses. Were recorded and solved IR, UV-VIS, RAMAN, MS, RMN and DRX spectra. All the elemental and spectral data are in accordance with the proposed structure.

Project’s web page: http://teclu.chem.uaic.ro/moldoveanu/contract-te/, was continuous updated with the scientific reports.

 A part of the obtained results were organized to be published in journals and presented on a series of national and international conferences as following:

Two published papers:

  1. D. Astefanei, N. Buzgar, M. Risca, C. Moldoveanu, I. Mangalagiu: „Synthesis, SERS, Raman and FT-IR investigation in conjunction with DFT theoretical simulations on N-(2-cyanoethyl)-imidazole. Part I”; Revista de Chimie, 65(6), 684-688, 2014. (ISSN: 0034-7752).
  2. Ghe. Zbancioc, I. Mangalagiu, C. Moldoveanu: Ultrasound assisted synthesis of imidazolium salts: an efficient way to ionic liquids; Ultrasonics Sonochem, 23(c), 376-384, 2015. DOI: 10.1016/j.ultsonch.2014.10.028.

One paper submited for publication:

  1. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, D. Maftei, I. Mangalagiu: The cycloaddition of the benzimidazolium ylides with alkynes: new mechanistic insights; Tetrahedron Letters, 56, xxx-xxx, 2015. (under review).

19 lucrari prezentate la conferinte nationale si internationale:

  1. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, V. Antoci. D. Maftei, I. Mangalagiu New mechanistic insights on the cycloaddition of the benzimidazolium ylides with alkynes Zilele Universitatii “Al. I. Cuza-Iasi“, 31 Octombrie – 1 Noiembrie 2014, (Poster ).
  2. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, V. Antoci. D. Maftei, I. Mangalagiu The cycloaddition of the benzimidazolium ylides with alkynes: mechanism elucidation XXXIII-rd Romanian Chemistry Conferance 1-3 october 2014, Calimaneşti-Caciulata, Valcea, Romania (Poster presentation P.S.I. 28).
  3. Ghe. Zbancioc, C. Moldoveanu, V. Antoci. D. Mantu, I. Mangalagiu IMIDAZOLIUM AND BENZIMIDAZOLIUM SALTS THROUGH ULTRASOUND ASSISTED SYNTHESIS  XXXIII-rd Romanian Chemistry Conferance 1-3 of October 2014, Calimaneşti-Caciulata, Valcea, Romania (Poster presentation P.S.I. 18).
  4. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, V. Antoci. I. Mangalagiu X-RAY STRUCTURE ELUCIDATION OF New Pyrrolo DERIVATIVES 14th International Balkan Workshop on Applied Physics 2-4 of July 2014, Constanta, Romania (Poster presentation S4 P12).
  5. Ghe. Zbancioc, C. Moldoveanu, A.M.. Zbancioc, G. Tataranga. I. Mangalagiu NEW PYRROLOQUINOXALINE COMPOUNDS: SYNTHESIS AND SPECTRAL ANALYSES 14th International Balkan Workshop on Applied Physics 2-4 of July 2014, Constanta, Romania (Poster presentation S4 P13).
  6. 6.      C. Moldoveanu, Ghe. Zbancioc, D. Mantu, V. Antoci. I. Mangalagiu Imidazolium salts as ionic liquids via ultrasound assisted synthesis The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova May 28-30 2014, Chisinau, Moldova (Poster presentation P 154).
  7. 7.      Ghe. Zbancioc, C. Moldoveanu, D. Maftei, D. Mantu, V. Antoci. I. Mangalagiu XRD structure elucidation of new fluorescent pyrrolo-imidazole derivatives The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova May 28-30 2014, Chisinau, Moldova (Poster presentation P 167).
  8. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, P. M. Stiuleac, I. O. Silea, I. Mangalagiu Sinteza de noi lichide ionice cu schelet imidazolic Zilele Universitatii “Al. I. Cuza-Iasi“, 31 Octombrie – 1 Noiembrie 2013, (Poster ).
  1. Ghe. Zbancioc, C. Moldoveanu, D. Maftei, V. Antoci, I. Mangalagiu: Sinteza şi elucidarea structurii unor noi derivati de pirrolo-imidazol fluorescenti Zilele Universitatii “Al. I. Cuza-Iasi“, 31 Octombrie – 1 Noiembrie 2013, (Poster ).
  2. Mantu, D.; Moldoveanu, C.; Zbancioc, G.; Antoci, V.; Stoian, I.; Mangalagiu, I.: „Synthesis of new ionic liquids imidazole based” XIV European Symposium on Organic Reactivity ESOR 2013, 1-6 September 2013, Prague, Czech Republic. (poster 69).
  3. Zbancioc, G.; Maftei D.; Moldoveanu, C.; Zbancioc, A.M.; Tataringa, G.; Mangalagiu, I.: „Synthesis and XRD Structure Elucidation of new Fluorescent Pyrrolo-imidazole” XIV European Symposium on Organic Reactivity ESOR 2013, 1-6 September 2013, Prague, Czech Republic. (poster 137)
  4. C. Moldoveanu, Ghe. Zbancioc, D. Mantu, I. Mangalagiu: NMR Study on structure elucidation of new imidazole ligands The XVII-th International Conference „Physical Methods in Coordination and Supramolecular Chemistry” (PPMCSC-XVII), Chisinau, 24 – 26 Octombrie 2012, (Poster P62).
  5. I. Stoian, P. M. Stiuleac, I. O. Silea, Ghe. Zbancioc, C. Moldoveanu, I. Mangalagiu: Ultrasound assisted synthesis of new imidazolium salts Zilele Universitatii “Al. I. Cuza-Iasi“, 25 – 26 Octombrie 2012, (Poster P29).
  6. Moldoveanu, C.; Zbancioc, Ghe.; Maftei, D.; Stoian, I.; Mangalagiu I.: „Synthesis of new imidazole derivarives possible ionic liquids using ultrasound irradiation”; XXXII-st Romanian Chemistry Conferance 3-5 october 2012, Calimaneşti-Caciulata, Valcea, Romania (Poster presentation P.S.I. 16).
  7. Moldoveanu, C.; Zbancioc, G.; Antoci, V.; Mangalagiu, I.: „Ultrasound assisted synthesis of new ionic liquids imidazole based” 11th International Conference on Global Research and Education Interacademia  27-30 August 2012, Budapest Hungary. (oral presentation)
  8. Zbancioc, G.; Moldoveanu, C.; Mantu D.; Mangalagiu, I.: „Microwave assisted synthesis of new highly fluorescent pyrrolo-imidazole” 11th International Conference on Global Research and Education Interacademia  27-30 August 2012, Budapest Hungary. (poster)
  9. Zbancioc, G.; Moldoveanu, C.; Stiuleac P. M.; Silea I. O.; Mangalagiu, I.: „Syhnthese de nouveaux pyrrolo-imidazole derives avec des prpprietes de fluorescence”; Septieme Colloque Franco-Roumain de Chimie Apliquee 27-29 juin 2012, Bacau, Roumanie (Poster 25, pp 70).
  10. Moldoveanu, C.; Zbancioc, G.; Stoian I.; Mangalagiu, I.: „Syhnthese assistee par ultrasons de nouveaux liquides ioniques  derives de l’imidazole”; Septieme Colloque Franco-Roumain de Chimie Apliquee 27-29 juin 2012, Bacau, Roumanie (Poster 13, pp 47).
  11. C. Moldoveanu, D. Astefanei, D. Maftei, Ghe. Zbancioc, I. Stoian, I. Mangalagiu: New imidazole based ionic liquids European Exhibition of Creativity and Innovation EURO INVENT, Iasi 12 – 14 May 2011, (Innovative Researches R.29.). Diploma of Excellence.

Based on the results obtained within the project we expect to publish at least two scientific articles in journals with high impact factor.

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