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Synthesis and properties of model push-pull systems based on indane-1,3-dione
Authors: Solanke Parmeshwar
Year: 2015
Type of publication: ostatní - dizertace
Publisher name: Univerzita Pardubice
Place: Pardubice
Page from-to: nestránkováno
Titles:
Language Name Abstract Keywords
cze Syntéza a vlastnosti mpdelových push-pull systémů na bázi indan-1,3.dionu Indan-1,2-dion byl vybrán jako základní stavební kámen pro nové push-pull molekuly. Systematickou obměnou substituentů na tomto skeletu bylo připraveno šestnáct cílových derivátů. Syntetické cesty zahrnovaly Knoevenagelovu kondenzaci a rovněž cross-couplingové reakce (Suzuki-Miyaura nebo Sonogashira). Připravené látky byly plně charakterizovány. Vztahy mezi strukturou a vlastnostmi byly studovány na základě naměřených fyzikálních parametrů a DFT kalkulací. push-pull deriváty, chromofory, indan-1,3-dion, nelineární optika, Knoevenagel kondenzace, Suzuki-Miyaura cross-coupling, Sonogashira cross-coupling
eng Synthesis and properties of model push-pull systems based on indane-1,3-dione This Ph.D. thesis focuses on indane-1,3-dione and its utilization in organic push-pull molecules. In the theoretical part are reviewed synthetic pathways leading to this diketone, its general reactivity and subsequent historical overview of its application in organic push-pull molecules, mostly as a terminal electron acceptor. Further modern applications of indane-1,3-dione derived molecules in optoelectronics are given as well. These especially include nonlinear optics, solar cells, organic light-emitting diodes and molecular glasses. Based on the literature survey, new indane-1,3-dione push-pull derivatives were proposed and designed. The new molecules represent (D-pi)2-A-pi-D push-pull chromophores in which indane-1,3- dione constitute a central acceptor modified by three peripheral donors. In this way, T-shaped molecules were gained. The indane-1,3-dione was modified with donors both at the C2 and newly also at the C4 and C7 positions. Sixteen new target molecules were synthesized and represent a first systematic modification of indane-1,3-dione fused benzene ring. The developed synthesis started from commercially available phthalanhydride, its iodination and transformation into 4,7-diiodoindane-1,3-dione intermediate in terms of Claisen condensation. This intermediate underwent Al2O3- or piperidine-catalyzed Knoevenagel condensation with 4-(N,N-dimethylamino)phenyl- and 5-(piperidin-1-yl)thiophene-substituted aldehydes. The peripheral donors were introduced via twofold Suzuki-Miyaura or Sonogashira cross-coupling reactions with boronic acids (pinacol esters) or terminal acetylenes. The molecular structure and purity of all target compounds and intermediates were determined by 1H- and 13C-NMR, MS, IR, elemental analyses and crystallography. Fundamental properties of these new chromophores were studied by X-ray analysis, electrochemistry, UV/Vis absorption spectra, and differential scanning calorimetry. push-pull derivatives, chromophores, indane-1,3-dione, nonlinear optics, Knoevenagel condensation, Suzuki-Miyaura cross-coupling, Sonogashira cross-coupling

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