Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures

Würthner, Frank

doi:10.1039/b401630k

Cited by 2,189 publications

(2,090 citation statements)

References 94 publications

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“…Furthermore, PDI redox potentials can be tuned, most effectively through substitutions at the "bay" (1,6,7,12) and/or "ortho" (2,5,8,11) positions, allowing them to be energetically matched to different active-layer and TCO materials. 25,26 In a recent study, 27 we began examining the properties of PDI monolayers tethered to ITO via phosphonic acid (PA) anchoring groups. ET rate constants exceeding 10 3 s -1 were measured for PDI-PA monolayers on ITO, and a dependence on the bridge length, which dictated the tunneling distance, was demonstrated.…”

Section: Introductionmentioning

confidence: 99%

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Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface

Zheng

Jradi

Parker

et al. 2016

ACS Appl. Mater. Interfaces

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Chemisorption of an organic monolayer to tune the surface properties of a transparent conductive oxide (TCO) electrode can improve the performance of organic electronic devices that rely on efficient charge transfer between an organic active layer and a TCO contact. Here a series of perylene diimides (PDIs) was synthesized and used to study relationships between monolayer structure/properties and electron transfer kinetics at PDI-modified indium tin oxide (ITO) electrodes. In these PDI molecules, one of the imide substituents is a benzene ring bearing a phosphonic acid (PA) and the other is a bulky aryl group that is twisted out of the plane of the PDI core. The size of the bulky aryl group and the substitution of the benzene ring bearing the PA were both varied which altered the extent of aggregation when these molecules were absorbed as monolayer films (MLs) on ITO, as revealed by both attenuated total reflectance (ATR) and total internal reflection fluorescence (TIRF) spectra. Polarized ATR measurements indicate that in these MLs, the long axis of the PDI core is tilted at an angle of 33˚-42˚ relative to the surface normal; the tilt angle increased as the degree of bulky substitution increased. Rate constants for electron transfer (k s,opt ) between these redox-active modifiers and ITO were determined by potential-modulated ATR spectroscopy. As the degree of PDI aggregation was reduced, k s,opt declined which is attributed to a reduction in the lateral electron self-exchange rate between adsorbed PDI molecules, as well as the heterogeneous conductivity of the ITO electrode surface. Photoelectrochemical measurements using a dissolved aluminum phthalocyanine as an electron donor showed that ITO modified with any of these PDIs is a more effective electron-collecting electrode than bare ITO.

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Section: Introductionmentioning

confidence: 99%

“…Although aggregation can be controlled by substitution at other positions, 28,29 the LUMO is characterized by a nodal plane that passes through the imide nitrogen atoms; 25 thus, in the absence of strong inductive effects, modifications can be made at these positions without simultaneously altering the energy levels of the PDI.…”

Section: Introductionmentioning

confidence: 99%

Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface

Zheng

Jradi

Parker

et al. 2016

ACS Appl. Mater. Interfaces

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“…General: 1 H and 13 C NMR spectra were recorded on a Bruker DPX-400 spectrometer (operating at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR) in CDCl 3 and [D 6 ]DMSO with tetramethylsilane as an internal standard. All spectra were recorded at 25 8C and coupling constants (J values) are given in Hz.…”

Section: Methodsmentioning

confidence: 99%

“…The dynamic nature of the equilibria governing the extent of polymerization provides enormous potential in manipulating the macroscopic properties of these polymers, whether in solution or in other phases. Recent studies in the groups of Würthner [13][14][15] and Schubert [16,17] established the viability of the terpyridylmetal coordinative bond as a promising strategy for the preparation of such self-assembled supramolecular polymers. In these studies, fluorescent supramolecular coordination polymers were obtained by utilizing terpyridyl-Zn II coordination.…”

Section: Introductionmentioning

confidence: 99%

Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers

Bozdemir

Büyükçakır

Akkaya

2009

Chemistry A European J

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Bright polymers: Fluorescent coordination polymers made up of versatile functionalized bodipy (boron‐dipyrrin) chromophore building blocks, such as that depicted, are described. Polymerization is signaled by changes in fluorescence emission intensity and shifts in peak emission wavelengths.magnified imageWe designed and synthesized novel boradiazaindacene (Bodipy) derivatives that are appropriately functionalized for metal‐ion‐mediated supramolecular polymerization. Thus, ligands for 2‐terpyridyl‐, 2,6‐terpyridyl‐, and bipyridyl‐functionalized Bodipy dyes were synthesized through Sonogashira couplings. These fluorescent building blocks are responsive to metal ions in a stoichiometry‐dependent manner. Octahedral coordinating metal ions such as ZnII result in polymerization at a stoichiometry corresponding to two terpyridyl ligands to one ZnII ion. However, at increased metal ion concentrations, the dynamic equilibria are re‐established in such a way that the monomeric metal complex dominates. The position of equilibria can easily be monitored by 1H NMR and fluorescence spectroscopies. As expected, although open‐shell FeII ions form similar complex structures, these cations quench the fluorescence emission of all four functionalized Bodipy ligands.

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“…Their electronic and optical properties can be significantly modified by variation of the substituents in the bay region (1, 6, 7 and 12 positions of perylene diimide unit) and/or in the N atoms of the diimide. 1,2 Due to these remarkable properties, PDIs are materials that, in additon to their use as industrial important pigments, 3 have been utilized or explored in other various optical and electronic applications, 4,5,6,7,8 or for liquid crystals, 9 and for highly fluorescent J-aggregates. 10 Also, the incorporation of metal centers to PDI structures at the imide region or at bay positions offers the possibility to modify the photochemistry and photophysics, and as a result their potential applications.…”

Section: Introductionmentioning

confidence: 99%

Highly fluorescent complexes with 3-isocyanoperylene and N-(2,5-di-tert-butylphenyl)-9-isocyano-perylene-3,4-dicarboximide

et al. 2014

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Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures

Abstract: Perylene bisimide dyes and their organization into supramolecular architectures through hydrogen-bonding, metal ion coordination and pi-pi-stacking is discussed; further self-assembly leading to nano- and meso-scopic structures and liquid-crystalline compounds is also addressed.

Cited by 2,189 publications

References 94 publications

Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface

Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface

Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers

Highly fluorescent complexes with 3-isocyanoperylene and N-(2,5-di-tert-butylphenyl)-9-isocyano-perylene-3,4-dicarboximide

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