1,3,6,8‐Tetraphenylpyrene Derivatives: Towards Fluorescent Liquid‐Crystalline Columns?

Abstract

Tetraphenylpyrene has been selected as a discotic core to promote liquid‐crystalline fluorescent columns in view of its high fluorescence quantum yield in solution and ease of substitution by flexible lateral side chains. The synthesis and characterization of ten new derivatives of pyrene have been carried out; the pyrene core has been substituted at the 1,3,6,8‐positions by phenylene rings bearing alkoxy, ester, thioether, or tris(alkoxy)benzoate groups on the para position; the compounds have been characterized by mass spectrometry and 1H NMR and UV‐vis spectroscopies. In order to generate liquid‐crystalline phases, the nature, number, and size of the side chains as well as the degree of polarity around the tetraphenylpyrene core have been varied. However, the desired liquid‐crystalline behavior has not been observed. The supramolecular order together with the absorption and emission properties in solution and the solid state are discussed and compared to theoretical predictions. Quantum‐chemical calculations rationalize the high solid‐state fluorescence of a tetraphenylpyrene derivative for which the crystal structure has been determined.

Electrofluorochromism in π-conjugated ionic liquid crystals

“…It is worth highlighting that compounds 1 and 2 exhibit high fluorescent quantum yields (F) either in the liquid crystalline phases or in the solid state at room temperature (Table 1), among the highest ever reported [19][20][21][22] .…”

“…However, the synthesis of fluorescent liquid crystal including ionic ones, is challenging because of aggregation-caused fluorescent quenching [19][20][21][22] . Thus, electrofluorochromic liquid crystals have not been reported yet.…”

Blue-Emitting Butterfly-Shaped 1,3,5,9-Tetraarylpyrenes: Synthesis, Crystal Structures, and Photophysical Properties

“…As a comparison, the aromatic aldehyde 4c was condensed with 4-tert-butylaniline to afford the Schiff base 5, and 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene (6) was synthesized according to the modified literature procedure. 13 The 7-tert-butyl-1,3,5,9-tetraarylpyrenes 4 were soluble in common organic solvents such as toluene, CH 2 Cl 2 , CHCl 3 , THF, acetonitrile, and N,N-dimethyl-formamide, and exhibited excellent thermal stability under air/N 2 . The key thermal data for the pyrene derivatives 4 are summarized in Table 1.…”

New method for the synthesis of a highly-conjugated acene material and its application in Perovskite solar cells

“…They have potential applications as active components in field-effect transistors, 1 photovoltaic devices, 2 light-emitting diodes, 3 and magnetic devices. 10 The pioneering work on PAHs was reported by Scholl, 4 Clar, 5 and Zander.…”