Large photoactive supramolecular ensembles prepared from C60–pyridine substrates and multi-Zn(ii)–porphyrin receptors

Trabolsi, Ali; Urbani, Maxence; Delgado, Juan Luis; Ajamaa, Fettah; Elhabiri, Mourad; Solladié, Nathalie; Nierengarten, Jean‐François; Albrecht‐Gary, Anne‐Marie

doi:10.1039/b712081h

Cited by 21 publications

(27 citation statements)

References 55 publications

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“…The latter observation clearly revealed that the presence of the fullerene subunit in 7 plays a key role in the observed cooperativity. Similar binding studies have been also carried out with hexaporphyrin 9Zn 6 and pyridine 7 (Figure ) . Job's plot provided evidence for 1:6 complex formation.…”

Section: Weak Intramolecular Interactions To Stabilize Supramolecusupporting

confidence: 61%

“…The binding behavior of pyridine 7 to ditopic receptor 5Zn 2 was also investigated in CH 2 Cl 2 by UV/Vis absorption and luminescence . As shown in Figure , divalent receptor 5Zn 2 has three possible states: fully bound [( 5Zn 2 ) · ( 7 ) 2 ], partially bound [( 5Zn 2 ) · ( 7 )] and free ( 5Zn 2 ).…”

Section: Weak Intramolecular Interactions To Stabilize Supramolecumentioning

confidence: 99%

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Weak Intramolecular Interactions to Stabilize Supramolecular Fullerene‐Porphyrin Conjugates and to Control the Conformation of Multiporphyrinic Arrays

Nierengarten

2019

Eur J Inorg Chem

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Porphyrins are key building blocks for the construction of photoactive supramolecular ensembles and molecular machines. As part of this research, our group is involved in a program on the development of supramolecular systems combining porphyrin building blocks with fullerene acceptors, and different strategies have been developed to obtain stable, non‐covalent conjugates. These results are described in the first part of this review with special emphasis on positive cooperative effects resulting from the existence of secondary weak intramolecular interactions in the supramolecular assemblies. On the other hand, our group has also developed multiporphyrinic arrays to generate supramolecular ensembles mimicking the primary events observed in the natural photosynthetic system, in particular light harvesting devices in which multiporphyrinic antenna collect light and channel the absorbed energy to a single energy acceptor. During this work, weak intramolecular coordination interactions have been observed between metalloporphyrins and triazole subunits allowing us to control the conformation of complex multiporphyrinic arrays. Based on this observation, we have designed molecular machines mimicking the blooming of a flower. These results are described in the second part of the present review.

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Section: Weak Intramolecular Interactions To Stabilize Supramolecusupporting

confidence: 61%

Section: Weak Intramolecular Interactions To Stabilize Supramolecumentioning

confidence: 99%

Weak Intramolecular Interactions to Stabilize Supramolecular Fullerene‐Porphyrin Conjugates and to Control the Conformation of Multiporphyrinic Arrays

Nierengarten

2019

Eur J Inorg Chem

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“…[22] Subsequently,t he compound class of porphyrin-HPBs expanded to al ibrary of extraordinary light-harvesting arrays. [22][23][24][25][26][27][28][29][30][31] Their oxidized derivatives, porphyrin-HBCs, [32][33][34][35][36][37][38][39][40][41] however,d id not evolve parallel to the discoveries of novel porphyrin HPBs, althought heir preparation seems to be the logical continuation of the HPB architectures.T he first directly linked porphyrin-HBC was reported in 2013, it was synthesized in an intramolecular oxidative cyclodehydrogenation reaction of the respective porphyrin-HPB. [33] The transformation, commonly known as "Scholl reaction", turns af lexible, nonconjugated HPB moiety into ap lanarized, aromatic HBC unit, which significantly influences the porphyrins'c haracteristics.…”

Section: Introductionmentioning

confidence: 99%

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Martin

Lungerich

Hampel

et al. 2019

Chemistry A European J

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Porphyrin–hexabenzocoronene architectures serve as good model compounds to study light‐harvesting systems. Herein, the synthesis of porphyrin functionalized hexa‐peri‐hexabenzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. A series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative coupling conditions. The transformation to the respective HBC derivatives worked well with mono‐ and tri‐porphyrin‐substituted HPBs. However, if more porphyrins are attached to the HPB core, Scholl oxidations are hampered or completely suppressed. Hence, a change of the synthetic strategy was necessary to first preform the HBC core, followed by the introduction of the porphyrins. All products were fully characterized, including, if possible, single‐crystal XRD. UV/Vis absorption spectra of porphyrin‐HBCs showed, depending on the number of porphyrins as well as with respect to the substitution pattern, variations in their spectral features with strong distortions of the porphyrins’ B‐band.

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“…It has been shown previously that the thermodynamic stability of BIPYC + p dimers induces positive shifts in the first redox potential, whereas the second reduction process leading to BIPY 0 is negatively shifted. [82] Interestingly, for HV 12 + &(CB7) 6 , no shift (DE 2 1=2 = 0 mV) was detected for the second reduction wave, which would normally be attributed to the transformation HV 6( C +) &(CB7) 6 ! HV 0 &(CB7) 6 .…”

Section: Reduction Of the [N]pseudorotaxanesmentioning

confidence: 94%

Radical‐Cation Dimerization Overwhelms Inclusion in [n]Pseudorotaxanes

Nono

Dalvand

Wadhwa

et al. 2014

Chemistry A European J

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Suppression of the dimerization of the viologen radical cation by cucurbit[7]uril (CB7) in water is a well-known phenomenon. Herein, two counter-examples are presented. Two viologen-containing thread molecules were designed, synthesized, and thoroughly characterized by (1)H DOSY NMR spectrometry, UV/Vis absorption spectrophotometry, square-wave voltammetry, and chronocoulometry: BV(4+), which contains two viologen subunits, and HV(12+), which contains six. In both threads, the viologen subunits are covalently bonded to a hexavalent phosphazene core. The corresponding [3]- and [7]pseudorotaxanes that form on complexation with CB7, that is, BV(4+)⊂(CB7)2 and HV(12+)⊂(CB7)6, were also analyzed. The properties of two monomeric control threads, namely, methyl viologen (MV(2+)) and benzyl methyl viologen (BMV(2+)), as well as their [2]pseudorotaxane complexes with CB7 (MV(2+)⊂CB7 and BMV(2+)⊂CB7) were also investigated. As expected, the control pseudorotaxanes remained intact after one-electron reduction of their viologen-recognition stations. In contrast, analogous reduction of BV(4+)⊂(CB7)2 and HV(12+)⊂(CB7)6 led to host-guest decomplexation and release of the free threads BV(2(·+)) and HV(6(·+)), respectively. (1)H DOSY NMR spectrometric and chronocoulometric measurements showed that BV(2(·+)) and HV(6(·+)) have larger diffusion coefficients than the corresponding [3]- and [7]pseudorotaxanes, and UV/Vis absorption studies provided evidence for intramolecular radical-cation dimerization. These results demonstrate that radical-cation dimerization, a relatively weak interaction, can be used as a driving force in novel molecular switches.

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Large photoactive supramolecular ensembles prepared from C60–pyridine substrates and multi-Zn(ii)–porphyrin receptors

Cited by 21 publications

References 55 publications

Weak Intramolecular Interactions to Stabilize Supramolecular Fullerene‐Porphyrin Conjugates and to Control the Conformation of Multiporphyrinic Arrays

Weak Intramolecular Interactions to Stabilize Supramolecular Fullerene‐Porphyrin Conjugates and to Control the Conformation of Multiporphyrinic Arrays

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Radical‐Cation Dimerization Overwhelms Inclusion in [n]Pseudorotaxanes

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