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T-Shaped (Donor-pi-)(2)Acceptor-pi-Donor Push-Pull Systems Based on Indan-1,3-dione
Authors: Solanke Parmeshwar | Bureš Filip | Pytela Oldřich | Klikar Milan | Mikysek Tomáš | Mager Loic | Barsella Alberto | Růžičková Zdeňka
Year: 2015
Type of publication: článek v odborném periodiku
Name of source: European Journal of Organic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 5339-5349
Titles:
Language Name Abstract Keywords
cze (Donor-pi-)(2)akceptor-pi-donor push-pull systém tvaru T na bázi indan-1,3.dionu. Bylo syntetizováno šestnáct cílových molekul ve tvaru T, ve kterých místo centrální akceptorní jednotky zastává indan-1,3-dion. Připravené push-pull molekuly byly charakterizovány rentgenostrukturní analýzou, NMR spektry, UV/Vis spektry, DSC kalorimetricky a byly uskutečněny DFT výpočty. Donor-acceptor systém; Chromofor; Elektrochemie; nelineární optika; DFT kalkulace
eng T-Shaped (Donor-pi-)(2)Acceptor-pi-Donor Push-Pull Systems Based on Indan-1,3-dione Sixteen model (donor-pi-)(2)acceptor-pi-donor [(D-pi-)(2)A-pi-D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push-pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all target molecules were investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed, and structure-property relationships were evaluated. Electron donors attached at the C-2 position through systems of various lengths affect the studied properties most significantly. The side donors at C-4 and C-7 can be described as auxiliary and do not dominate the observed properties. However, thiophene is a more efficient donor than N,N-dimethylaniline in this respect. Hence, indan-1,3-dione bearing a piperidylthiophene donor connected through a propenylidene spacer at C-2 completed with two side thiophen-2-ylethynyl branches at C-4 and C-7 showed the highest figure of merit among the studied properties. Donor-acceptor systems; Chromophores; Electrochemistry; Nonlinear optics; Density functional calculations

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