27 / 2023-07-28 23:05:15

SYNTHESIS AND STRUCTURE-PROPERTIES RELATIONSHIPS OF P-CONTAINING POLYMETHINE CYANINES

Dyes,polymethine,conjugaison,ylide,Phosphonium

New Technologies in Phosphorus Chemistry > 1) New reagents and methods in organophosphorus Chemistry

Many cyanine have been reported and used for various of applications either in biomedicine or in material science ^[1] . Cyanine dyes have the particularity to have a full charge delocalization on an odd number of C-sp² between two lateral nitrogen (Fig. 1). This particular structure, called the ideal polymethine state (IPS) leads to characteristic optical properties. Since the 60’s, some rare examples of P-containing cyanine dyes ^[2-4] were reported but the lack of synthetic access did not allowed their democratization like classical cyanine. Furthermore, there are no proofs that an IPS is reached with those structure. 



In this work, we will describe our efforts to synthesize different P-containing polymethine cyanines We will also systematically study their structures and optical properties to evaluate if these “phospha-cyanines” possess the structural and spectroscopic properties of cyanines in their IPS. 



Reference:

[1] Bouit, P.-A.; Aronica, C.; Toupet, L.; Le Guennic, B.; Andraud, C.; Maury, O. J. Am. Chem. Soc. 2010, 132, 4328−4335

[2] Depoorter, H.; Nys, J.; van Dormael, A.Tetrahedron Letters 1961, 6, 199-205



[3] Weimei, L; Zhenghua, Z; Zhuguang,Y; Mengzhen, H; Bingkui, W, Dyes Pigm. 1990, 14, 211-216



[4] Yamada,S; Ishii, E; Konno, T; Ishihara, T, Org. Biomol. Chem, 2007, 5, 1442-1449