Zn-porphyrin/Zn-phthalocyanine dendron for SWNT functionalisation

Hy, Le Ho Khanh; Rivier, Lucie; Jousselme, Bruno; Jégou, Pascale; Filoramo, Arianna; Campidelli, Stéphane

doi:10.1039/c0cc02704a

Cited by 41 publications

(8 citation statements)

References 33 publications

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“…The X-ray photoelectron absorption spectroscopy confirmed the coordination of Zn to porphyrin rings. As shown in Figures e and S1 in the SI, the 2p 3/2 and 2p 1/2 orbital peaks of Zn in P-HMZnP, S-HMZnP, and nonhollow MZnP were observed in 1022.3 and 1045.3 eV, respectively, which matches with those reported for Zn–tetraphenylporphyrins in the literature . Solid-phase 13 C nuclear magnetic resonance spectroscopy (NMR) on P-HMZnP, S-HMZnP, and nonhollow MZnP showed 13 C peaks at 120.6, 131.0, 143.3, and 150.2 ppm, corresponding to Zn–porphyrin rings (Figure S4 in the SI).…”

supporting

confidence: 84%

Hollow and Microporous Zn–Porphyrin Networks: Outer Shape Dependent Ammonia Sensing by Quartz Crystal Microbalance

Park

Hong

et al. 2015

Chem. Mater.

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S Supporting Information R ecently, various microporous organic networks (MONs) have been prepared by coupling reactions of organic building blocks. 1−4 For example, the Cooper research group and others have shown that the Sonogashira coupling of rigid organic building blocks results in the formation of various MON materials. 1−3,5 These materials have shown unique physical properties such as high surface area and microporosity (pore size <2 nm). 1−5 On the basis of these properties, the MON materials have been applied as gas adsorbents 1−7 and sensing materials 1,8,9 for small guests. By using tailored building blocks, various sensing moieties can be introduced into MON materials. For example, metallo-porphyrins with vacant axial coordination sites have been incorporated into MON materials to interact with guest molecules. 10−14 In these applications, the small molecules diffuse into MON materials to interact with inner active moieties. To reduce the diffusion pathway of guest molecules, our research group has studied the hollow structure engineering of MON materials based on nontemplate 15 or template methods. 16 Quartz crystal microbalance is a very useful device for gas sensing. 17 Various inorganic and organic polymeric materials have been used as sensing materials in QCM devices. 17 The porous sensing materials can enhance efficiency because the inner active species can be utilized in the sensing. 18 Although MON materials have promising potential as sensing materials, as far as we are aware, their application to QCM devices has not been reported. MON materials prepared without templates usually have irregular shape and size. In our preliminary studies on the application of nonhollow and irregular MON granules bearing metallo-porphyrins to QCM devices, the materials showed very poor performance as sensing materials. In this work, we report the synthesis of hollow and microporous Zn−porphyrin networks (HMZnP) with controlled outer shapes and their shape dependent ammonia sensing performance in QCM devices. Figure 1 shows a synthetic route for the shape controlled HMZnP materials. For preparation of polyhedral HMZnP (P-HMZnP), polyhedral ZIF-8 nanocrystals were prepared by procedures in the literature. 19,20 Microporous (metal-free) porphyrin network (MP) was formed on the surface of ZIF-8 via the Sonogashira coupling of tetrakis(4-ethynylphenyl)porphyrin with 1,4-diiodobenzene (See Experimental Sections in the Supporting Information, SI). The inner ZIF-8 in ZIF-8@MP was completely etched by treatment of hydrochloric acid to form hollow and microporous porphyrin networks with a polyhedral shape (P-HMP). The reaction of P-HMP with zinc acetate resulted in the P-HMZnP. When Zn−porphyrin building blocks with four terminal alkynes were used instead of metal-free porphyrins, the Zn in porphyrin was decoordinated during the acidic etching process. Thus, the Zn was introduced to P-HMP by post-synthetic modification. Spherical HMZnP (S-HMZnP) was prepared using silica nanospheres as templates, instead of ZIF-8 nanocr...

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supporting

confidence: 84%

Hollow and Microporous Zn–Porphyrin Networks: Outer Shape Dependent Ammonia Sensing by Quartz Crystal Microbalance

Park

Hong

et al. 2015

Chem. Mater.

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“…In addition, as suggested by molecular modeling, several conformations between the carbon nanotube surface and the porphyrin unit in solution may also result in broadening of the 1 ‐centered Soret band. Apart from the above changes, no other significant differences have been observed for the hybrid materials 13, 31…”

Section: Resultsmentioning

confidence: 86%

CNTs in Optoelectronic Devices: New Structural and Photophysical Insights on Porphyrin‐DWCNTs Hybrid Materials

Aurisicchio

Marega

Corvaglia

et al. 2012

Adv Funct Materials

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The preparation and physical characterization of diverse porphyrin‐derived double‐walled carbon nanotubes (DWCNTs) conjugates are described. A porphyrin molecule is covalently linked and physically adsorbed to COOH‐derived DWCNTs. The photophysical properties of all porphyrin‐CNTs derivatives are studied in solution and in polymeric matrices. Definitive experimental evidence for photoinduced electron and/or energy transfer processes involving the porphyrin chromophores and the CNT wall is not obtained, but solid‐state UV‐vis absorption profiles display electronic transitions fingerprinting J‐ and H‐ type aggregates, where porphyrin molecules intermolecularly interact “head‐to‐tail” and “face‐to‐face”, respectively. In parallel, molecular modeling based on force‐field simulations is performed to understand the structure of the porphyrin‐CNTs interface and the nature of the interactions between the porphyrins and the DWCNTs. Finally, multilayered‐type devices are fabricated with the aim of investigating the interaction of the porphyrin‐derived DWCNTs with poly(3‐hexylthiophene)‐pyrene matrices containing small amounts of 1‐[3‐(methoxycarbonyl)propyl]‐1‐phenyl‐[6.6]C61.

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“…The photophysics of the resulting SWNT–Zn(II) porphyrin conjugates 192.3 were investigated and the lifetimes of the charge-separated states were determined. A SWNT functionalized with a Zn(II) porphyrin–Zn(II) phthalocyanine dendron was also obtained through a click reaction . Graft-polymer-like carbon nanotubes functionalized with porphyrin polymers were also prepared .…”

Section: Reactions At Alkenes and Alkynes Bound To Porphyrinsmentioning

confidence: 99%

Synthesis and Functionalization of Porphyrins through Organometallic Methodologies

2016

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This review focuses on the postfunctionalization of porphyrins and related compounds through catalytic and stoichiometric organometallic methodologies. The employment of organometallic reactions has become common in porphyrin synthesis. Palladium-catalyzed cross-coupling reactions are now standard techniques for constructing carbon-carbon bonds in porphyrin synthesis. In addition, iridium- or palladium-catalyzed direct C-H functionalization of porphyrins is emerging as an efficient way to install various substituents onto porphyrins. Furthermore, the copper-mediated Huisgen cycloaddition reaction has become a frequent strategy to incorporate porphyrin units into functional molecules. The use of these organometallic techniques, along with the traditional porphyrin synthesis, now allows chemists to construct a wide range of highly elaborated and complex porphyrin architectures.

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Zn-porphyrin/Zn-phthalocyanine dendron for SWNT functionalisation

Abstract: SWNT-porphyrin/phthalocyanine conjugates are described and fully characterised; their optical and electrochemical properties are investigated.

Cited by 41 publications

References 33 publications

Hollow and Microporous Zn–Porphyrin Networks: Outer Shape Dependent Ammonia Sensing by Quartz Crystal Microbalance

Hollow and Microporous Zn–Porphyrin Networks: Outer Shape Dependent Ammonia Sensing by Quartz Crystal Microbalance

CNTs in Optoelectronic Devices: New Structural and Photophysical Insights on Porphyrin‐DWCNTs Hybrid Materials

Synthesis and Functionalization of Porphyrins through Organometallic Methodologies

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