Abstract
Two new classes of dendrimers bearing 8 and 32 fluorene donor groups have been synthesized. The first and second generations of these porphyrin-PAMAM-fluorene dendrimers were characterized by 1H-NMR, 13C-NMR, FTIR, UV-vis spectroscopy, elemental analyses and MALDI-TOF mass spectrometry. The UV-vis spectra showed that the individual properties of donor and acceptor moieties were preserved, indicating that the new dendrimers could be used as photosynthetic antennae. Furthermore, for fluorescent spectroscopy, these dendrimers showed good energy transfer.
Highlights
In the last few years, porphyrin-core dendrimer systems have been attracting much attention because the terminal substituent groups on the photoactive core can modulate their physico-chemical properties [1,2,3,4]
The addition between the hydroxy groups of the porphyrin was conducted with methyl bromoacetate in acetone and K2CO3 (Scheme 1)
When the dendrimers are excited at 420 nm in the Soret band, the emission spectra reveal a strong red fluorescence with a peak maximum at 653 nm and a weak shoulder at 716 nm (Figure 2c) and almost no residual emission of the fluorene for both compounds
Summary
In the last few years, porphyrin-core dendrimer systems have been attracting much attention because the terminal substituent groups on the photoactive core can modulate their physico-chemical properties [1,2,3,4] This has been extensively studied for a number of different applications, such as: Molecules 2015, 20 shape-selective catalysts [3], organic solar cells [4], photoelectrochemical devices [5], light-emitting diodes [6], photodynamic therapy [7], chemical sensors [8], optical limiters [9], and so forth. Poly(amidoamine) (PAMAM) species are a novel class of commercial dendrimers which possess an established molecular composition with different terminal functional groups. These macromolecules were first synthesized and investigated by Tomalia [1]. In this paper we report on the synthesis and characterization of some new modified first and second generation PAMAM derivatives using diethylenetriamine-bearing fluorene fluorescent units at their peripheries and their photophysical characteristics
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