Crown ether functionalization of a porphyrin-based “molecular square”: induction of fluorescence sensitivity to alkali metal cations

Chang, Seung Hyun; Chung, Kwang Bo; Slone, Rovert V.; Hupp, Joseph T.

doi:10.1016/s0379-6779(00)00367-2

Cited by 23 publications

(15 citation statements)

References 12 publications

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“…265 The nanoscale cavities of these prophyrin assemblies were chemically tailored for incorporation of receptor groups with high affinities for specific ions or molecules. 266,267 For example, the edge-funtionalized supramolecular square, 268 244 , derived from 2,8,12,18-tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(4-pyridyl)-porphyrin ( 243 ) and Re(CO) 5 Cl (Scheme 56) renders lattices of 244 responsive to aqueous Zn(II) ions upon cavity functionalization with tris(2-aminoethyl)amine, whereas functionalization with 1,6-hexanedithiol enhanced the lattice response to molecular iodine by a mechanism involving formation of a charge-transfer complex. 266,267 Fabrication of these porphyrinic squares as thin membrane films led to size-selective transport and thus they act as a nanofilters for various probe molecules.…”

Section: Two-dimensional (2d) Ensemblesmentioning

confidence: 99%

“…266,267 For example, the edge-funtionalized supramolecular square, 268 244 , derived from 2,8,12,18-tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(4-pyridyl)-porphyrin ( 243 ) and Re(CO) 5 Cl (Scheme 56) renders lattices of 244 responsive to aqueous Zn(II) ions upon cavity functionalization with tris(2-aminoethyl)amine, whereas functionalization with 1,6-hexanedithiol enhanced the lattice response to molecular iodine by a mechanism involving formation of a charge-transfer complex. 266,267 Fabrication of these porphyrinic squares as thin membrane films led to size-selective transport and thus they act as a nanofilters for various probe molecules. 269 Photoelectrochemical cells based on these cavity-containing porphyrinic molecular squares were able to sensitize flat indium-tin oxide (ITO) electrodes to photocurrent production with visible light.…”

Section: Two-dimensional (2d) Ensemblesmentioning

confidence: 99%

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Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles

2011

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Section: Two-dimensional (2d) Ensemblesmentioning

confidence: 99%

Section: Two-dimensional (2d) Ensemblesmentioning

confidence: 99%

Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles

2011

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“…27 Films and membranes displaying molecularscale porosity was generated from squares 22 and 23 by van der Waals aggregation, layer-by-layer assembly chemistry based on zirconium-phosphonate links or polymerization at liquid-liquid interfaces. 25 In addition to molecular sieving, the films, membranes 28 and free assemblies of Re(I) bridged porphyrin squares 18-23 have been used for chemical sensing, 27 oxidative catalysis 29 and light-to-electrical conversion. 12…”

Section: Re(i) Bridged Porphyrin Tetradsmentioning

confidence: 99%

Re(I) bridged porphyrin dyads, triads and tetrads

Yedukondalu

Ravikanth

2011

J Chem Sci

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Porphyrin rings containing two meso-pyridyl groups either in cis or trans fashion can be used to construct Re(I) bridged multiporphyrin assemblies. The cis-dipyridyl porphyrins with various porphyrin cores such as N 4 , N 3 O, N 3 S, N 2 S 2 have been used to react with Re(CO) 5 Cl in THF at refluxing temperature and constructed planar Re(I) bridged porphyrin dyads containing either one type of porphyrin subunit or two types of porphyrin subunits. The trans-dipyridyl porphyrins have been used to construct Re(I) bridged porphyrin squares. The porphyrin dyads have been explored for singlet-singlet energy transfer studies and porphyrin squares have been used for catalysis, chemical sensing, molecular sieving and photocurrent production studies. An overview of synthesis of Re(I) bridged porphyrin dyads, triads and tetrads and their interesting photophysical properties are highlighted in this paper.

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“…More than 100 cavity variants, including several chiral variants, have been prepared in this way. In illustrative experiments, modest selectivity for alkali metal ions, Zn 2+ , and molecular iodine as guest species has been observed [32,33]. An alternative approach that is a focus of current work is to gate the entry of guests into extended square channels by appropriately functionalizing channel termini, rather than cavities (channel interiors).…”

Section: Self-assembled Porphyrin Squares As Catalysts and Sensorsmentioning

confidence: 99%

A perspective on four new porphyrin-based functional materials and devices

Drain

Hupp

Suslick

et al. 2002

J. Porphyrins Phthalocyanines

115

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The tremendous potential for the manifold applications of porphyrins, porphyrazines, and phthalocyanines derives from their photophysical and electrochemical properties, their remarkable stability, and their predictable and rigid structure. These applications include nonlinear optics, catalysts, sensors, actuators, molecular sieves, and therapeutics. All of these properties are modulated by appending various chemical moieties onto the macrocycles, by choice of metallo derivative, and by the choice of environment. In multichromophoric systems, furthermore, the relative orientation of the chromophores, the nature of the linker, and the size of the system also dictate the properties. The synthesis of multichromophoric systems -both via covalent and noncovalent linkers -is driven by the desire to make new materials and to understand biological processes such as the various aspects of photosynthesis. Though electron and energy transfer processes continue to drive the synthesis of ever more complex systems, more recent focus has shifted toward other applications and functionalities of these structures. The focus of this perspective is on four recent developments in formation and characterization of functional, porphyrinic materials and devices: (1) self-assembly and self-organization of porphyrin arrays and aggregates into phototransistors and photonic devices;(2) self-assembled porphyrin squares for sensors, sieves, and catalysts; (3) covalently bound arrays of different chromophores as photonic materials; and (4) spatially separated arrays of metalloporphyrins as cross-reactive sensors.

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Crown ether functionalization of a porphyrin-based “molecular square”: induction of fluorescence sensitivity to alkali metal cations

Cited by 23 publications

References 12 publications

Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles

Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles

Re(I) bridged porphyrin dyads, triads and tetrads

A perspective on four new porphyrin-based functional materials and devices

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