Study of a Convenient Method for the Preparation of Hydrosoluble Fluorescent Triazatruxene Derivatives

Abstract

Triazatruxene derivatives find many applications as lipophilic compounds, but few examples of hydrosoluble derivatives have been reported so far. In this paper, we compare different synthetic routes for the preparation of hydrophilic triazatruxene derivatives and define the most versatile path-way. The synthesized compounds are fluorescent not only in organic solvents, as reported for other lipophilic derivatives, but also in water, making them particularly suitable for biological applications

New indole trimers as precursors for molecular electronic materials

“…In this context, we previously reported the formation of 2,3,7,8,12,13-hexabromo-5,10,15-trihydroindolo [3,2-a,3',2'-c]carbazole (1) ( Figure 1, also called hexabromotriazatruxene) by the simple reaction of three equivalents of Br 2 with indole. 5 This represents a straightforward route to a large, conjugated π-system containing readily-substituted Br and N-H groups and has stimulated much subsequent work to prepare a large number of derivatives (Figure 1), [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] studied for their photophysical, liquid crystal and/or charge-transport properties. In particular, such trigonal aromatic molecules offer enhanced opportunities in the formation of dendritic molecules 18,20 or discotic liquid crystalline systems 9 in comparison with linear analogues.…”

Octupolar (C3 and S4) Symmetric Cyclized Indole Derivatives: Syntheses, Structures, and NLO Properties

“…As shown in Scheme , we synthesized the Tr (yield 18.2%) and TTr (yield 5.5%) by trimerizing and tetramerizing the indolin-2-one monomer in the presence of POCl 3 in a one-pot reaction at 100 °C for 8 h under Ar atmosphere. The low yield of TTr may be the reason why TTr failed to be noticed in the previous synthesis of Tr . We successfully grew the crystal of Tr, and the X-ray structure (Figure and Table ) demonstrated the C 3 h -symmetric octupolar skeleton of the Tr molecule, but its crystal is centrosymmetric ( P 2 1 / c ).…”

Fluorescent glycoconjugates and their applications

“…Star-shaped fluorescent glycoclusters, mainly triazatruxenebased and triphenylamine-conjugated, have been constructed for fluorescence detection of lectins. For their intrinsic photophysical and redox properties as well as their π-stacking capability, 180 triazatruxene derivatives have been considerably interested especially as potential light-emitting diodes, [181][182][183] batteries and capacitors. 184 Similarly, considering their high photoluminescence and electroluminescence efficiencies, triphenylamine-based conjugates have been used for several applications including the development of optoelectronic devices 185,186 and fluorescent sensor materials.…”