Highly fluorescent and electroactive molecular squares containing perylene bisimide ligands

Würthner, Frank; Sautter, Armin

doi:10.1039/a909892e

Cited by 203 publications

(90 citation statements)

References 15 publications

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“…Hydrogen bond donating solvents in this case do not cause especially large shifts, as they do in 1. Similar spectral shifts were observed in studies of the binding between melamine and perylene imides by Würthner et al [15,16] They attributed this effect to the polarization of the imide carbonyl groups by hydrogen bonding. In their case the shifts are smaller than in the rotaxanes discussed here.…”

supporting

confidence: 55%

“…[15,19,20] The separation between the reduction and oxidation waves is about 80 mV, which is only slightly larger than the theoretically expected 60 mV for a reversible process. The presence of the wheel changes the redox behavior of the perylene core.…”

mentioning

confidence: 73%

“…The spectra of the radical anion and the dianion of the axle 1 and the [2]rotaxane 2 are similar to the spectra observed for similar perylene diimide derivatives. [15,19,20] The absorption maxima and estimated molar absorption coefficients are shown in Table 6. The molar absorption coefficients were estimated using the coefficients measured for the axle 1 and [2]rotaxane 2 in chloroform and assuming full conversion of the Table 5.…”

mentioning

confidence: 99%

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Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

Baggerman

Jagesar

Vallée

et al. 2007

Chemistry A European J

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[2]- and [3]-rotaxanes with a tetraphenoxy perylene diimide core were synthesized. Hydrogen bonding between the wheel and the imide changes the optical properties of the perylene chromophore: the absorption and fluorescence spectra are red-shifted. The decay times of the rotaxanes are shorter in comparison with that of the axle. Single molecule fluorescence measurements reveal relatively narrow distributions of emission maxima and decay times. The averages are in agreement with ensemble measurements. The observed red shifts make the perylene diimide a suitable chromophore for sensing the position of the wheel on the axle.

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confidence: 55%

mentioning

confidence: 73%

mentioning

confidence: 99%

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Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

Baggerman

Jagesar

Vallée

et al. 2007

Chemistry A European J

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“…The left-handed screw is a result of chiral induction by sugar moieties present in the components. Numerous synthetic assemblies that contain multiple chromophores in a cyclic (10)(11)(12)(13) or polymeric array (14-17) have been reported. However, none of them can match natural assemblies in the sense that they are both molecularly well defined and display (chir)optical properties that are different from the separate components.…”

mentioning

confidence: 99%

Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly

Prins

Thalacker

Würthner

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

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Multichromophoric hydrogen-bonded assemblies 13⅐(BAR)6 are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV͞visible (Vis) absorption maximum (⌬ max ‫؍‬ 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10 ؊4 M). The determined C50% values of 2-3 M in benzene show the extremely high stability of these hydrogen-bonded assemblies. Most chromophores are susceptible to changes in their optical properties depending on their chemical environment. This principle has been actively exploited for the development of optical sensors (1-3) and devices (4-6). Along these lines, Nature generates a wide variety of different fruit and floral colors from different noncovalent complexes of the natural anthocyanin chromophores (7,8). These colors cover almost the complete visible spectrum, despite the fact that the structural diversity in the building blocks is surprisingly low. Commelinin is a blue complex in which a total of six anthocyanins and six flavocommelins are pairwise coordinated around two central magnesium cations (Fig. 1a) (9). The blue color of commelinin is a direct result of the self-assembly process driven by coordination of the anthocyanins to magnesium and completely disappears on dissociation of the complex. In addition, commelinin is strongly CD active as a result of exciton coupling between the stacked anthocyanin units (Fig. 1b). The left-handed screw is a result of chiral induction by sugar moieties present in the components. Numerous synthetic assemblies that contain multiple chromophores in a cyclic (10-13) or polymeric array (14-17) have been reported. However, none of them can match natural assemblies in the sense that they are both molecularly well defined and display (chir)optical properties that are different from the separate components. In this paper we report hydrogen-bonded assemblies that bear a remarkably close resemblance to commelinin ( Fig. 1 c and d). The similarity is not only expressed by the supramolecular structure, but also by a similar change in both the optical and chiroptical properties of the chromophores on formation of the assembly. These spectral changes enable us to study the stability of these assemblies at micromolar concentrations, far below the 1 H NMR sensitivity threshold.The barbiturate BAR has a chromogenic donor--acceptor system with a charge-transfer (CT) absorption band in the visible range at max ϭ 478 nm in chloroform ( 478 ϭ 8. ) (Fig. 3a). Evidence for the quantitative formation of assembly 1 3 ⅐(BAR) 6 was obtained from 1 H NMR spectroscopy in CDCl 3 . The spectrum shows the characteristic ...

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“…Considerable interest in organic-inorganic hybrid photoluminescent materials has been paid due to their potential applications in lighting, analytical probes and lasers [23,24]. The fluorescent properties of 1 have been investigated in aqueous solution.…”

Section: Tablementioning

confidence: 99%

Synthesis, structure, ion-exchange and fluorescence of a novel two-dimensional niobium fluorophosphate with 4.8-net layer

Feng

Qiu

Zhong

et al. 2011

Inorganic Chemistry Communications

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Highly fluorescent and electroactive molecular squares containing perylene bisimide ligands

Abstract: Large functional molecular squares have been assembled with ditopic perylene bisimide bridging ligands and Pt(II) and Pd(II) phosphine corner units and their optical, electrochemical and spectroelectrochemical properties have been studied.

Cited by 203 publications

References 15 publications

Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly

Synthesis, structure, ion-exchange and fluorescence of a novel two-dimensional niobium fluorophosphate with 4.8-net layer

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