Molecularly Defined Shape‐Persistent 2D Oligomers: The Covalent‐Template Approach to Molecular Spoked Wheels

Mössinger, Dennis; Hornung, Jens; Lei, Shengbin; Feyter, Steven De; Höger, Sigurd

doi:10.1002/anie.200701614

Cited by 64 publications

(33 citation statements)

References 55 publications

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“…[99] Numerous further investigations have been reported in the field of self assembled monolayers. [100]- [102] Shape persistent two dimensional oligomers such as spoked wheels [103] as well as shape persistent macrocycles based on a phenyl ethynyl backbone have been immobilized on graphite. [104]- [106] In Figure 5 the deposition from solution to the surface of highly oriented pyrolytic graphite (HOPG) is shown.…”

Section: Adsorption On Graphitementioning

confidence: 99%

Shape‐Switchable Azo‐Macrocycles

et al. 2009

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The synthesis of four shape‐switchable macrocycles comprising different peripheral substituents is described. The macrocycles 1–4 consist of m‐terphenyl semicircles interlinked by two azo joints. These macrocycles were assembled from nitro‐functionalized m‐terphenyl moieties through reductive dimerization. The semicircles were assembled through Suzuki cross‐coupling reactions. The molecular weights of the macrocycles were determined by vapour pressure osmometry, because mass spectrometry failed in the cases of 2 and 3. The E → Z photoisomerization reactions were analysed by UV/Vis spectroscopy complemented by 1H NMR studies. A very slow thermal back‐reaction indicated considerable stabilization of the Z isomer. The reduced efficiency of the thermal back‐reaction probably arises from the reduced degree of freedom due to the mechanical interlinking of the two azo groups. The photostationary state consisted of all‐Z (85 %) and all‐E isomers (15 %). The E → Z transformation induced by irradiation displayed simple exponential kinetics, which indicates pairwise switching of the two azo groups in a macrocycle, at least on the timescale under investigation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Adsorption On Graphitementioning

confidence: 99%

Shape‐Switchable Azo‐Macrocycles

et al. 2009

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“…As shown in Scheme , compound 1 was synthesized from HPB by using a known procedure 11. Snowflake‐shaped luminophore BPT was prepared (yield of the isolated product: 51 %) by a six‐fold Suzuki coupling reaction from 1 and monoboronic acid of TPE ( 2 ) with [Pd(PPh 3 ) 4 ] as catalyst and aqueous NaOH solution as base.…”

Section: Resultsmentioning

confidence: 99%

“…The other materials were of the common commercial level and used as received. Hexakis(4‐bromophenyl)benzene ( 1 )11 and 4‐(1,2,2‐triphenylvinyl)phenylboronic acid ( 2 )6a were synthesized according to the literature methods. Thin layer chromatography (TLC) was conducted on flexible sheets precoated with SiO 2 and the separated products were visualized by using UV light.…”

Section: Methodsmentioning

confidence: 99%

Hexaphenylbenzene‐Based, π‐Conjugated Snowflake‐Shaped Luminophores: Tunable Aggregation‐Induced Emission Effect and Piezofluorochromism

Chang

Jing

Cong

et al. 2015

Chemistry A European J

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In this work, two rigid, multiple tetraphenylethene (TPE)-substituted, π-conjugated, snowflake-shaped luminophores BT and BPT were facilely synthesized by using a 6-fold Suzuki coupling reaction. These molecules are constructed based on the nonplanar structure of propeller-shaped hexaphenylbenzene (HPB) or benzene as core groups and TPE as end groups. As a result, they reserve the intrinsic aggregation-induced emission (AIE) property of the TPE moiety. Meanwhile, both fluorescence quantum yield and piezochromic behavior in the solid state can be tuned or switched by inserting the phenyl bridges through changing the twisting conformation. The more extended structure BPT showed a much stronger AIE effect and higher ΦF,f in the solid state in comparison with that of BT. Furthermore, an excellent optical waveguide application of these molecules was achieved. However, the revisable piezofluorochromic behavior has only appeared when BT was ground using a pestle and treated with solvent.

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“…6,7 Increasing interest in p-conjugated macrocycles is attributed to the their promising application in material science, 8 host-guest systems, 9 storage devices, 10 digital computation, 11 and molecular rotors. [12][13][14] We previously reported the synthesis and physicochemical characterization of benchmark macrocycle 1 and BODIPYphenylacetylene macrocycle 2a (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%