Efficient Host–Guest Energy Transfer in Polycationic Cyclophane–Perylene Diimide Complexes in Water

Ryan, Seán T. J.; Barrio, Jesús del; Ghosh, Indrajit; Biedermann, Frank; Lazăr, Alexandra; Lan, Yang; Coulston, Roger J.; Nau, Werner M.; Scherman, Oren A.

doi:10.1021/ja5032437

Cited by 95 publications

(53 citation statements)

References 74 publications

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“…The same group also reported the self-assembly of tetracationic cyclobis(4,4′-(1,4-phenylene)bispyridine-p-phenylene)tetrakis(chloride) (ExBox) and dicationic PBIs supramolecular complexes. 246 These complexes showed efficient energy transfer from ExBox (donor) to PBIs (acceptor) and underwent further complexation with two neutral cucurbit [7]uril (CB [7]) at the outer quaternary ammonium moieties to form 3-polypseudorotaxane.…”

Section: Organization Of Core-unsubstituted Pbis In the Bulk Solid Statementioning

confidence: 99%

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

et al. 2015

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CONTENTS 1. Introduction 962 1.1. Prologue 962 1.2. Parent Perylene Bisimide Chromophore 963 1.3. Core-Substituted Perylene Bisimides 964 1.4. Perylene Bisimides in the Solid State 966 1.5. Areas of Application 966 2. Linear, Dendritic, and Macrocyclic Covalent PBI Ensembles 968 2.1. Excitonic Coupling and Deactivation Processes of Photoexcited PBIs 969 2.2. Rigid PBI Dimers 971 2.3. Flexible PBI Ensembles 974 2.4. Cyclic PBI Ensembles 976 3. π-Stacked PBI Assemblies 979 3.1. Self-Assembly of Core-Unsubstituted PBIs in Solution 979 3.2. Organization of Core-Unsubstituted PBIs in the Bulk Solid State 984 3.3. Self-Assembly of Amphiphilic PBIs in Aqueous Media and Solid Bulk State 987 3.4. Self-Assembly of Core-Substituted PBIs 991 3.5. Self-Assembly of Dye Arrays Composed of Multiple PBIs 995 3.6. Self-Assembly of Multichromophoric PBI Conjugates Containing Other Dyes 996 4. Hydrogen-Bond Directed Self-Assembly 1000 4.1. Self-Assembly Directed by Imide−Imide H-Bonding Interactions 1000 4.2. Self-Assembly Directed by Side-Chain Amide−Amide H-Bonding Interactions 1003 4.3. Self-Assembly Directed by Other H-Bonding Interactions 1006 4.4. Coassembly Directed by Imide−Melamine H-Bonding Interactions 1008 4.5. Coassembly Directed by Melamine−Cyanurate/Barbiturate H-Bonding Interactions 1011

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Section: Organization Of Core-unsubstituted Pbis In the Bulk Solid Statementioning

confidence: 99%

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

et al. 2015

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“…1,2 These properties have led to their exploitation in various applications such as organic field-effect transistors, chemical sensors, 3 thin-film transistors, 4 complex supramolecular systems 5,6 and, increasingly, organic photovoltaics (OPVs). 7 Recent interest in OPVs has begun to outstrip that of traditional silicon based solar cells due to their low cost, synthetic adaptability and processing ability.…”

Section: Thionated Perylene Diimides With Intense Absorbance In the Nmentioning

confidence: 99%

Thionated perylene diimides with intense absorbance in the near-IR

et al. 2016

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“…FL 490 555 [246] thioflavin (ThT) (free dye f = 0.06) [131,250] perylene monoimide(PMI) (f = 0.22, bound) [129] berberine chloride (BC) CB7 water (pH 7)…”

Section: 84mentioning

confidence: 99%

Chemical Sensors Based on Cucurbit[n]uril Macrocycles

Sinn

Biedermann

2018

Israel Journal of Chemistry

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147

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Cucurbit[n]urils (CBn) are glycoluril‐based macrocyclic hosts that bind many biologically, medicinally and environmentally relevant analytes with record high affinities in aqueous media. They are therefore prime candidates for the design of chemosensors that are operational in biological fluids, waste and drinking water and have promising potential to be utilized for in vitro and in vivo sensing and imaging applications. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, they are chemically robust and they show a desired fast analyte‐binding kinetics. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, are chemically robust and show a desired fast analyte‐binding kinetics Selective analyte detection and differentiation is possible owing to the charge‐ and size‐selective binding characteristics of the CBn members and due to the wide range of cyclic and acyclic CBn derivatives that differ in their analyte binding preference. Because CBn hosts are spectroscopically silent in the visible electromagnetic spectrum, optical signal transduction with CBn based chemosensing ensembles is typically performed by indicator displacement assays (IDA), which are easy to implement and applicable to both aliphatic and aromatic analytes. The extension to array‐based sensing with CBn chemosensors is straightforward. Associative binding assays (ABA), which are uniquely available with CB8‐based self‐assembled receptors offer superior analyte differentiation possibility due to emerging spectral fingerprints in the absorbance, circular dichroism (CD) and emission spectra for the receptor•analyte complexes. Direct signal generation is promising for inherently spectroscopically active analytes, for instance through absorbance, CD, emission and surface enhanced Raman spectroscopy (SERS). Sensitive NMR (19F, 129Xe) techniques, electron spin resonance (ESR), redox, and mass spectrometry are also valuable signal transduction options for specific analytes. CBn based chemosensors were successfully utilized for the monitoring of biophysical processes and enzymatic reactions with label free analytes or substrates in real time. These applications capitalize on the fast equilibration kinetics of CBn‐analyte complexes and the bio‐compatibility of CBn hosts. The tabulated large body of data extracted from reported CBn‐based binding studies is hoped to provide the reader with a valuable starting point for designing practically applicable CBn‐based sensors.

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Efficient Host–Guest Energy Transfer in Polycationic Cyclophane–Perylene Diimide Complexes in Water

Cited by 95 publications

References 74 publications

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

Thionated perylene diimides with intense absorbance in the near-IR

Chemical Sensors Based on Cucurbit[n]uril Macrocycles

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