Selective ratiometric pH-sensing PAMAM light-harvesting dendrimer based on Rhodamine 6G and 1,8-naphthalimide

Abstract

The paper reports on the divergent synthesis and fluorescence characteristics of a polyamidoamine (PAMAM) dendron of second generation. Novel compound is configured as a light harvesting antenna where the system surface is labeled with yellow-green emitting 4-(N-piperazinyl)-1,8-naphthalimide "donor" units capable of absorbing light and efficiently transferring the energy to a focal Rhodamine 6G "acceptor". The energy transfer is calculated to 82%. Furthermore, the 1,8-naphthalimide periphery of the system is designed on the "fluorophore-spacer-receptor" format and is able to act as a molecular fluorescence photoinduced electron transfer based probe. Due to the both effects, photoinduced electron transfer in the periphery of the system and pH dependent rhodamine core absorption, novel antenna is able to act as a highly selective ratiometric pH fluorescence probe. Thus, the distinguishing features of light-harvesting systems (fluorescence resonance energy transfer) were successfully combined with the properties of classical ring-opening sensor systems. © 2013 Elsevier B.V.