An easy access to porphyrin triads and their supramolecular interaction with a pyridyl [60]fulleropyrrolidine

Costa, Joana I. T.; Farinha, Andreia S.F.; Neves, Maria G. P. M. S.; Tomé, Augusto C.

doi:10.1016/j.dyepig.2016.02.035

Cited by 18 publications

(12 citation statements)

References 53 publications

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“…Upon addition of PyC 60 to a solution of 6 in toluene, the fluorescence intensity decreased significantly when exciting at 428 nm, as depicted in Figure 6. These changes are fully consistent with strong interactions between the photoexcited 6 and PyC 60 in the 6 –PyC 60 complex [68,70,73]. The fluorescence quenching of the precursor Zn 2 and diporphyrin 4 upon addition of PyC 60 was also observed (Figures S15 and S17 in the ESI).…”

Section: Resultssupporting

confidence: 73%

“…The addition of PyC 60 to a solution of 6 in toluene induced a decrease of the Soret band (at 422 nm) along with the appearance of an isosbestic point at 428 nm (Figure 4). This suggests the formation of a 6 –PyC 60 complex, presumably via axial coordination of the pyridyl group to the zinc porphyrin (Figure 5), as reported in similar systems [56,68,69,70,71,72].…”

Section: Resultssupporting

confidence: 71%

“…The para -fluorine atoms are selectively substituted by the nucleophile and mono- to tetra-substituted porphyrin derivatives may be obtained. We have reported the synthesis of multiporphyrin compounds via nucleophilic aromatic substitution of fluorine atoms in porphyrin 2 [20] or hexafluorobenzene [67,68]. Using a similar approach, herein we present a simple procedure for the preparation of diporphyrins and pentaporphyrins.…”

Section: Introductionmentioning

confidence: 99%

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A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine

et al. 2019

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A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)–PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6–PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.

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Section: Resultssupporting

confidence: 73%

Section: Resultssupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

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A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine

et al. 2019

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“…Double substitutions have previously been described for reactions of low molar mass PFB derivatives with amines. [64][65][66][67] In fact, Costa et al 64 Despite the unexpected side reactions the modification of pPFBMA with amines has potential in producing 'smart' polymers. The modification of pPFBMA with di-and tri(ethylene glycol) methyl ether amine (Table 4 Entries 6, 7) resulted in water insoluble products.…”

Section: Polymer Modification: Aminesmentioning

confidence: 99%

Para-Fluoro Postpolymerization Chemistry of Poly(pentafluorobenzyl methacrylate): Modification with Amines, Thiols, and Carbonylthiolates

et al. 2017

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A methacrylic polymer undergoing highly efficient para-fluoro substitution reactions\ud is presented. A series of well-defined poly(2,3,4,5,6-pentafluorobenzyl methacrylate) (pPFBMA)\ud homopolymers with degrees of polymerization from 28 to 132 and Ð ≤ 1.29 was prepared by the\ud RAFT process. pPFBMA samples were atactic (with triad tacticity apparent in 1H and 19F NMR\ud spectra) and soluble in most organic solvents. pPFBMA reacted quantitatively through parafluoro\ud substitution with a range of thiols (typically 1.1 equiv thiol, base, RT, < 1h) in the absence\ud of any observed side reactions. Para-fluoro substitution with different (thio)carbonylthio\ud reagents was possible and allowed for subsequent one-pot cleavage of dithioester pendent groups\ud with concurrent thia-Michael side group modification. Reactions with aliphatic amines (typically\ud 2.5 equiv amine, 50–60 °C, overnight) resulted in complete substitution of the para-fluorides\ud without any observed ester cleavage reactions. However, for primary amines, H2NR, double\ud substitution reactions yielding tertiary (–C6F4)2NR amine bridges were observed, which were\ud absent with secondary amine reagents. No reactions were found for attempted modifications of\ud pPFBMA with bromide, iodide, methanethiosulfonate, or thiourea, indicating a highly selective\ud reactivity toward nucleophiles. The versatility of this reactive platform is demonstrated through\ud the synthesis of a pH-responsive polymer and novel thermoresponsive polymers: an\ud oligo(ethylene glycol)-functional species with an LCST in water and two zwitterionic polymers\ud with UCSTs in water and aqueous salt solution (NaCl concentration up to 178 mM)

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“…Similar quenching results have been reported in both coordination supermolecule and porphyrin derivatives attached to a fullerene structure in organic solvents, while in such supramolecular formed via coordination interaction and pseudorotaxane association, dozens to hundred equivalents of fullerene derivative were needed to reach a majority of quenching of donor uorescence. 15,48 In the absence of block copolymer, the uorescence titration of ZnTPPS solution on increasing addition of mC 60 in water was also investigated (Fig. S11 †).…”

Section: Spectroscopic Properties Of Micellesmentioning

confidence: 99%

Zinc porphyrin/fullerene/block copolymer micelle for enhanced electron transfer ability and stability

Wang

Chen

et al. 2017

RSC Adv.

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An easy access to porphyrin triads and their supramolecular interaction with a pyridyl [60]fulleropyrrolidine

Cited by 18 publications

References 53 publications

A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine

A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine

Para-Fluoro Postpolymerization Chemistry of Poly(pentafluorobenzyl methacrylate): Modification with Amines, Thiols, and Carbonylthiolates

Zinc porphyrin/fullerene/block copolymer micelle for enhanced electron transfer ability and stability

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