Synthesis and Solvatochromatic properties of 9-(4-Aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene

Abstract

9-(4-Aminophenylethynyl)-10-(4-nitrophenylethynyl)anthracene (2) was synthesized in high yield by using a route involving sequential Sonogashira cross coupling reactions of 9-bromo-10-iodoanthracene with 4-nitrophenylacetylene and 4-aminophenylacetylene. Solvatochromism was observed in the absorption and fluorescence spectra of 2 in a variety of solvents. In less polar solvents, such as hexane and benzene, the fluorescence emission band of 2 appears in the green to orange region while this substance does not fluoresce in polar solvents, such as acetonitrile and DMF.

Two-Dimensional Covalent Organic Framework–Graphene Photodetectors: Insight into the Relationship between the Microscopic Interfacial Structure and Performance

“…The monomer 4 was synthesized according to the reported methods. 46 All the solvents are of ACS grade unless otherwise noted.…”

A simple and efficient synthesis of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene

“…Using tris(2,4,6-trimethylphenyl)phosphine (P(2,4,6-triMeC 6 H 2 ) 3 ) as a bulky, electron-rich ligand [18] instead of PPh 3 , compound 3a was obtained in a high yield of 92% (Table 1, entry 6). Among all the solvents we used here, the polar solvent DMF [20] resulted in good reactivity, giving 3a in 92% yield within 2.5 h (Table 1, entry 6), whereas other solvents, for example tetrahydrofuran (THF), toluene, and dioxane gave no cross-coupling products even after 24 h (Table 1, entries 7-9).…”

Dynamic covalent chemistry of imine polymers at the liquid/solid interface investigated by scanning tunneling microscopy

“…The monomer 4 was synthesized with reported method. 33 To ensure solubilization of all compounds, precursors were rst dissolved in dimethyl sulfoxide (1 mg g À1 ) and diluted with octanoic acid to obtain the desired concentration. For STM characterization, the monomers were mixed with desired molar ratios prior deposition onto the surface.…”