Naslov
Solvent-free and solution based synthesis of o- hydroxy imines with non-planar molecular geometry

Autori
Zbačnik, Marija ; Twigge, Linette ; Roodt, Andreas ; Cinčić, Dominik

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Acta Crystallographica Section A ; Abstracts of the 29th European Crystallographic meeting ; Rovinj, Croatia, August 2015 / - : IUCr Journals, Wiley, 2015, S464-s465

Skup
29th European Crystallographic meeting

Mjesto i datum
Rovinj, Hrvatska, 23.08.2015. - 28.08.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Solvent-free synthesis; o-Hydroxy Schiff bases; Structure-property correlation; Thermochromism

Sažetak
Solvent-free methods of synthesis (neat, liquid-, seeding-, ion-assisted grinding) have been recognised as faster, environmentally more friendly and economically more acceptable ways to prepare new but also already known compounds.[1] o-Hydroxy Schiff bases are well known organic compounds that can possess photo- and/or thermochromic properties in the solid state due to possibility of keto-enol tautomeric change via intramolecular O・・・N hydrogen bond.[2] They can be easily obtained by condensation of aldehydes (or ketones) and primary amines[3] and thereafter used as ligands in coordination chemistry of transition metals.[4] For the reason of their ability to reversibly change their colour upon changing external conditions their structure- property correlation has been extensively studied. For almost 30 years it was thought that Schiff bases with non-planar molecular geometry cannot show thermochromism[2] so much work was done in the past 20 years to find ones that do.[5] Herein, we report solvent-free and solution based syntheses of o-hydroxy Schiff bases with non- planar geometry obtained from salycilaldehyde and its derivatives and α-aminodiphenylmethane. The successfulness of method used was studied by means of PXRD, DSC and TG thermal analysis and NMR. Their thermochromic properties were checked by repeated exposure to temperature change from room to liquid-nitrogen temperature. The supramolecular impact on the keto-enol tautomerism (Figure 1) was studied using SCXRD. [1] S.L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Friščić, F. Grepioni, K.D.M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. Guy Orpen, I.P. Parkin, W.C. Shearouse, J.W. Steedk and D.C. Waddelli, Chem. Soc. Rev., 2012, 41, 413. [2] M.D. Cohen and G.M.J. Schmidt, J. Phys. Chem., 1962, 66, 2442 ; M.D. Cohen, G.M.J. Schmidt and S. Flavian, J. Chem. Soc., 1964, 2041 ; M.D. Cohen, Y. Hirshberg and G.M.J. Schmidt, J. Chem. Soc., 1964, 2051. [3] Schiff, H ; Ann. Chim., 1864, 131, 118. [4] A. Blagus, D. Cinčić, T. Friščić, B. Kaitner and V. Stilinović, Maced. J. Chem. Int. Ed., 2010, 29, 117. [5] E. Hadjoudis, M. Vittorakis and I.M. Mavridis, Tetrahedron, 1987, 43, 1345 ; F. Robert, A.D. Naik, B. Tinant, R. Robiette and Y. Garcia, Chem. - Eur. J., 2009, 15, 4327 ; F. Robert, P.-L. Jacquemin, B. Tinant and Y. Garcia, CrystEngComm, 2012, 14, 4396 ; B. Kaitner and M. Zbačnik, Acta Chim. Slov., 2012, 59, 670 ; M. Zbačnik and B. Kaitner, CrystEngComm, 2014, 16, 4162.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA