Facile synthesis of a flexible tethered porphyrin dimer that preferentially complexes fullerene C70

Jurow, Matthew J.; Farley, Christopher; Pabon, Cesar; Hageman, Brian; Dolor, Aaron; Drain, Charles Michael

doi:10.1039/c2cc31340e

Cited by 14 publications

(16 citation statements)

References 38 publications

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“…The significantly larger association constant of 1 for C 70 versus C 60 ( K C60 / K C70 =678) further revealed that cyclic bisporphyrin 1 is effective for selective C 70 inclusion. The value is also significantly higher than those of previously reported,, fullerene receptors (Table S2). Fascinated by this excellent ability of 1 to bind C 70 , we investigated the selective extraction of C 70 from C 60 /C 70 fullerene mixtures.…”

Section: Resultscontrasting

confidence: 65%

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture

Mondal

Rath

2017

Chemistry An Asian Journal

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An adaptable cyclic porphyrin dimer with highly flexible linkers has been used as an artificial molecular container that can efficiently encapsulate various aromatic guests (TCNQ/C /C ) through strong π-π interactions by adjusting its cavity size and conformation. The planar aromatic guest (TCNQ) can be easily and selectively exchanged with larger aromatic guests (C /C ). During the guest-exchange process, the two porphyrin rings switch their relative orientation according to the size and shape of the guests. This behavior of the cyclic container has been thoroughly investigated by using UV/Vis spectroscopy, NMR spectroscopy, and X-ray crystal structure determination of the host-guest assemblies. The electrochemical and photophysical studies demonstrated the occurrence of photoinduced electron transfer from bisporphyrin to TCNQ/C /C in the respective host-guest assemblies. The cyclic host can form complexes with C and C with association constants of (2.8±0.2)×10 and (1.9±0.3)×10 m , respectively; the latter value represents the highest binding affinity for C reported so far for zinc(II) bisporphyrinic receptors. This high selectivity for the binding of C versus C allows the easy extraction and efficient isolation of C from a C /C fullerene mixture. Experimental evidence was substantiated by DFT calculations.

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Section: Resultscontrasting

confidence: 65%

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture

Mondal

Rath

2017

Chemistry An Asian Journal

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“…26). 51 Upon mixing the dimer with C 60 and C 70 we discovered that it preferentially binds with fullerene C 70 over C 60 in toluene solution. The dimer–fullerene complex also forms stable aggregates when casted on glass.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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“…For example, disrupting the uniformity of the system or over-modifying a fullerene derivative may undermine its electric and biomedical properties. 6 It is particularly noted that the optimization of one organic device is relatively complex. Herein, we have developed a facile approach to optimize a photodetector device simply by substituting the traditional substrate with wavelength matched photonic crystals (PCs).…”

Section: Introductionmentioning

confidence: 99%

Improving the photo current of the [60]PCBM/P3HT photodetector device by using wavelength-matched photonic crystals

Xue

et al. 2014

J. Mater. Chem. C

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Facile synthesis of a flexible tethered porphyrin dimer that preferentially complexes fullerene C70

Abstract: A simple, high yield, two-step synthesis yields a porphyrin dimer linked by a flexible dithiol tether that preferentially binds fullerene C70 over C60 in toluene solution. The complex forms stable aggregates when cast on glass.

Cited by 14 publications

References 38 publications

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Improving the photo current of the [60]PCBM/P3HT photodetector device by using wavelength-matched photonic crystals

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Facile synthesis of a flexible tethered porphyrin dimer that preferentially complexes fullerene C70

Abstract: A simple, high yield, two-step synthesis yields a porphyrin dimer linked by a flexible dithiol tether that preferentially binds fullerene C70 over C60 in toluene solution. The complex forms stable aggregates when cast on glass.

Cited by 14 publications

References 38 publications

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C70 from a Fullerene Mixture

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C70 from a Fullerene Mixture

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Improving the photo current of the [60]PCBM/P3HT photodetector device by using wavelength-matched photonic crystals

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A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture

A Tunable Cyclic Container: Guest‐Induced Conformational Switching, Efficient Guest Exchange, and Selective Isolation of C₇₀ from a Fullerene Mixture