1 Sétif 16/02/2019 Disorder effect on optical properties of chiral structures, single crystal X-ray diffraction and DFT calculations 1 Laboratoire d'Electrochimie.

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1 1 Sétif 16/02/2019 Disorder effect on optical properties of chiral structures, single crystal X-ray diffraction and DFT calculations 1 Laboratoire d'Electrochimie des Matériaux Moléculaires et des complexes LEMMC, Université Ferhat Abbas Sétif 1, Sétif. 2 Emerged material unit, university of Setif, Setif 19000, Algeria International Conference on Materials Science 2018 (ICMS2018) Louiza Ouksel 1, Riadh Bourzami 2

2 16/02/20192 Aims Synthesis and characterization of new molecular materials Novel physicochemical properties

3 Synthesis Name of the compoundFormula R % Diéthyl [Hydroxy (Phényl) Méthyl] Phosphonate DHPMPC 11 H 17 O 4 P 70 Diéthyl [Hydroxy (4-MethoxyPhényl) Méthyl] Phosphonate DH4MPMPC 12 H 19 O 5 P 75 616/02/2019 RT Two molecules were synthesized via chemical reaction of benzaldehyde, triethyl phosphite at room temperature with a presence of catalyst

4 Characterization 1 H NMR spectroscopy 16/02/20197 IR spectroscopy

5 5 P-0-C P=O P-0-C P=0 Ar-O-C Without With 16/02/2019

6 6 ppm(t1) 10.0 5.0 0.0 4.03 CH21.22 CH3 1.15 CH3 3.75 Ar-O-CH3 Without With 1 H NMR spectroscopy 16/02/2019 3.94 CH2 IR and 1 H NMR Prove the good purity of materials

7 Crystallographic studies 16/02/20197

8 8 Without Appearance of synthesized products With 16/02/2019

9 9 Crystallographic study Empirical formulaC12H19O5P Crystal system Space groupP21/n a (Å)9,293 (5)10.606(16) b (Å)8,103 (5)7.83(9) c (Å)17,542 (5)18.292(3) β (°)95,329 (5)105.226(17) V (Å 3 )1315,2 (4)1466.5(4) Z Molecular weigth (g/mol) 244.23273.235 C 11 H 17 0 4 P Monoclinic 4 4 unit cell 16/02/2019 Without With Radical induced an increasing in volume

10 Intermolecular bonds Hydrogen bonds ensure the union between the molecules D—H···A D—HH···AD···AD—H···A O(4)—H(24)···O(5) 0.822 Å2.009Å2.701 Å130.6° Distances and angle of hydrogen bonds 10 16/02/2019

11 11 3D Network construction Without With

12 12 UV-Visible spectroscopy Polarimetry Optical properties 16/02/2019

13 13 UV-Visible spectroscopy WithoutWith (nm)258274  (l.mol -1.cm -1 ) 176266783 (nm) Cut off 292297 274 nm 258 nm Absorbanc e 16/02/2019 UV Lumière Light Without With HOMO LUMO E HOMO (eV) E LUMO (eV) ∆E gap (eV) η (eV) χ (eV) σ (eV) -1 ω (eV) Without -7,15-1,415.742,874,280,343,19 With -6,71-1,125.592,793,920,352,76 Good optical transmission transmission Strongabsorption affect a possibility to be UV to be UV protector on protector onglasses Transition

14 22 Stereochemistry and rotary power of light Composés Rotat ( °.dm -1.g -1.cm 3 )(-) 0,1(-) 0,2 Stereochemistry Stereochemistry (DFT) SS  Source lumineuse Lumière ordinaire Polariseur Lumière polarisé Plan a subi une rotation Observateur Chiral molecules  origin of the optical activity of the solution. Without With 16/02/2019 Unpolarized Light source polarizer polarized plan rotation observer

15 Network crystalline chirality 15 Possibility of combination between molecular and network crystalline chirality y x Chirality chain 16/02/2019 Chiral axis along Z direction

16 16/02/2019 16 TGA/TDA Thermalproperties Thermal properties 16/02/2019

17 17 Thermogravimetric study 159°C 194°C 93°C 187°C 265°C 376°C 477°C O-CH3 P-C-C p Without With 16/02/2019 TGA and TDA thermograms

18 16/02/2019L.E.M.MC18 Conclusion Two chiral molecular structures were synthesized. Two chiral molecular structures were synthesized. SXRD analyzes reveal that the structures crystallize in the same system. SXRD analyzes reveal that the structures crystallize in the same system. Radical increase the disorder. Radical increase the disorder. Chirality of molecules and the chirality of crystal lattices are combined. Chirality of molecules and the chirality of crystal lattices are combined. Polarimetry measurement and the UV-Vis spectroscopy proves a good optical properties. Polarimetry measurement and the UV-Vis spectroscopy proves a good optical properties. TGA-TDA proves a good thermal properties. TGA-TDA proves a good thermal properties.

19 16/02/201919 Perspectives Following optical properties Trials with other radicals

20 16/02/201920 Thank you for your attention