A diminoisoindoline-tetraphenylporphyrin (as Zn complex) unit has been used as building block for the preparation of a tetraphenylporphyrin-1,3-bis(2-pyridylimino)isoindoline conjugate (3). The chelating system of this molecule possesses two different binding centers. The optimization of the synthetic procedure allowed to obtain the ZnTPP-BPI moiety in very good yields, the structure of which was identified by means of UV/Vis, NMR, mass and X-ray methods. The Zn-porphyrin complex was then subject to Zn ion removal from the porphyrin core, allowing the isolation of the corresponding free base derivative. The optical features of the compound are very interesting, as expected from the fusion of two chromophores active in the UV and visible regions of the optical spectrum; this has also been confirmed by testing ZnTPP-BPI (3) as chemosensor for metal cations detection.
Joining Chromophores: a Porphyrin-BPI Fused System / Pomarico, Giuseppe; Mando, Federica; Lvova, Larisa; Lippolis, Vito; Fronczek, Frank R.; Smith, Kevin M.; Di Natale, Corrado; Paolesse, Roberto. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2019:4(2019), pp. 655-659. [10.1002/ejoc.201801553]
Joining Chromophores: a Porphyrin-BPI Fused System
Pomarico, Giuseppe
Primo
;
2019
Abstract
A diminoisoindoline-tetraphenylporphyrin (as Zn complex) unit has been used as building block for the preparation of a tetraphenylporphyrin-1,3-bis(2-pyridylimino)isoindoline conjugate (3). The chelating system of this molecule possesses two different binding centers. The optimization of the synthetic procedure allowed to obtain the ZnTPP-BPI moiety in very good yields, the structure of which was identified by means of UV/Vis, NMR, mass and X-ray methods. The Zn-porphyrin complex was then subject to Zn ion removal from the porphyrin core, allowing the isolation of the corresponding free base derivative. The optical features of the compound are very interesting, as expected from the fusion of two chromophores active in the UV and visible regions of the optical spectrum; this has also been confirmed by testing ZnTPP-BPI (3) as chemosensor for metal cations detection.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
