Publication detail

Triphenylamine-based fluorophores bearing peripheral diazine regioisomers. Synthesis, characterization, photophysics and two-photon absorption

Year: 2022

Type of publication: článek v odborném periodiku

Name of source: Dyes and Pigments

Publisher name: Elsevier Science

Place: Oxford

Page from-to: 110230

Titles:

Language	Name	Abstract	Keywords
cze	Trifenylaminové fluorofory nesoucí koncové diaziny. Syntéza, charakterizace, fotofyzikální vlastnosti a dvoufotonová absorpce	Byla připravena série šesti tripodálních fluoroforů s D-(pi-A3) uspořádáním. Struktura derivátů obsahuje centrální elektronově donorní trifenylaminový skelet a postranní elektronakceptorní diaziny (pyridazin, pyrimidin, pyrazin) vázané přes ethynylenové můstky. Příprava je založena na trojnásobném Sonogashirově cross-couplingu z výchozího tris(4-ethynylfenyl)aminu. Struktura látek byla potvrzena rentgenostrukturní analýzou. Termální a elektrochemické vlastnosti byly zkoumány s pomocí DSC a cyklické voltametrie. Dále byla použita UV-Vis absorpční spektroskopie a 2 PA analýza. Experimentální výśledky byly konfrontovány s výsledky DFT kalkulací.	trifenylamin; pyridazin; pyrimidin; pyrazin; regioizomery; tripodální fluorofory; dvoufotonová absorpce
eng	Triphenylamine-based fluorophores bearing peripheral diazine regioisomers. Synthesis, characterization, photophysics and two-photon absorption	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.	triphenylamine; pyridazine; pyrimidine; pyrazine; diazines; regioisomers; tripodal fluorophores; two-photon absorption

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