Journal
DYES AND PIGMENTS
Volume 201, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2022.110230
Keywords
Triphenylamine; Pyridazine; Pyrimidine; Pyrazine; Diazines; Regioisomers; Tripodal fluorophores; Two-photon absorption
Funding
- European Regional development Fund [CZ.02.1.01/0.0/0.0/16_025/0007445]
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A series of new push-pull fluorophores with D-(pi-A3) arrangement were designed and synthesized, and their structure-property relationships were revealed through experimental and theoretical studies.
A series of six tripodal push-pull fluorophores with D-(pi-A3) arrangement has been designed and synthesized. The structure of these fluorophores consists of a central electron-donating triphenylamine core and peripheral electron-withdrawing diazine units (pyridazine, pyrimidine, and pyrazine moieties), which are linked by an ethynylene pi-spacer. The preparation of the fluorophores involves threefold Sonogashira cross-coupling reaction starting from the key tris(4-ethynylphenyl)amine intermediate. The structure and spatial arrangement of two fluorophores were completely confirmed by X-ray analysis. Thermal and electrochemical behavior of prepared fluorophores were investigated by differential scanning calorimetry and cyclic voltammetry. Their linear optical properties were examined by UV-Vis absorption, steady-state and time resolved fluorescent spectroscopy while 2 PA analysis was used for a study of the nonlinear optical response. Experimental data were supported by DFT calculations. Based on the experimental as well as theoretical data, structure-property relationships have been thoroughly revealed.
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