Most known perylene diimides are lipophilic, with few exceptions of hydrophilic derivatives. Even in the latter case, the compounds have limited water solubility and show a strong tendency to self-aggregation. In this paper we present the synthesis of four new perylene derivatives with three and four basic side chains, obtained by functionalizing the bay-area of perylene. These molecules show great solubility in aqueous media as hydrochlorides and their tendency to self-aggregate is remarkably reduced with respect to the previously synthesized two-chained perylene diimides. Their different spectroscopic properties in various solvents and conditions are reported and discussed. (C) 2007 Elsevier Ltd. All rights reserved.
Synthesis and spectroscopic properties of highly water-soluble perylene derivatives / Alvino, Antonello; Marco, Franceschin; Chiara, Cefaro; Borioni, Silvia; Ortaggi, Giancarlo; Bianco, Armandodoriano. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 63:33(2007), pp. 7858-7865. [10.1016/j.tet.2007.05.096]
Synthesis and spectroscopic properties of highly water-soluble perylene derivatives
ALVINO, Antonello;BORIONI, SILVIA;ORTAGGI, Giancarlo;BIANCO, Armandodoriano
2007
Abstract
Most known perylene diimides are lipophilic, with few exceptions of hydrophilic derivatives. Even in the latter case, the compounds have limited water solubility and show a strong tendency to self-aggregation. In this paper we present the synthesis of four new perylene derivatives with three and four basic side chains, obtained by functionalizing the bay-area of perylene. These molecules show great solubility in aqueous media as hydrochlorides and their tendency to self-aggregate is remarkably reduced with respect to the previously synthesized two-chained perylene diimides. Their different spectroscopic properties in various solvents and conditions are reported and discussed. (C) 2007 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
