Synthesis of Fréchet-type dendritic homotriptycenes

Liu, Wenjie; Cao, Derong; Gao, Chunmei; Jiang, Yuyang; Meier, Herbert

doi:10.1007/s11426-009-0088-x

Cited by 4 publications

(3 citation statements)

References 44 publications

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“…Basic methods, like halogen exchange for a [F 18 ]fluoride anion, in the presence of Kryptofix [222], have been used in the labelling of nifedipine derivatives, 110 benzodiazepine receptors 111 and 6-fluoro-3,4-dihydroxy-L-phenylalanine 112 (this compound can also be labelled 113 by the use of [F 18 ]difluorine gas). Many new methods utilise nucleophilic attack by the [F 18 ]fluoride anion on 'good leaving groups' (such as tosyl or triflate) 114,115 this strategy has been used in the labelling of 2 116 -or 6 117 -[F 18 ]-6-deoxy-D-glucose and PBR111 118 (used for imaging a translocator protein). 2-iodo-4 0 -[F 18 ]fluorobenzophenone 119 was made in a similar way by a nucleophilic aromatic substitution, and this compound utilized to make a labelled peroxisome receptor-gamma ligand.…”

Section: Carbon (C 11 and C 14 )mentioning

confidence: 99%

Radiochemistry

Urch¹

2010

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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Section: Carbon (C 11 and C 14 )mentioning

confidence: 99%

Radiochemistry

Urch¹

2010

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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“…Alternatively, Walborsky et al [42] reacted anthraquinone with a Grignard reagent to generate anthranol derivatives, which were subjected to acid-catalyzed ring closure to form bridgeheadfunctionalized triptycenes. Furthermore, using the appropriate anthracenol derivatives, this dehydration-cyclization provided a novel bicyclo [3,2,2]octatriene, namely, homotriptycene (Figure 1, middle), which contains a new -CH 2group on the bridged ring of the classic triptycene [43][44][45][46][47][48][49]. Unfortunately, the lack of efficient procedures for the development of such diverse 3D scaffolds has limited the development of homotriptycene and other iptycene isomers; only a few iptycene-based materials have been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Spiro-fused bicyclo[3,2,2] octatriene-cored triptycene: synthesis, molecular packing, and functional aggregates

et al. 2021

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Aggregate science has led to the existence of functional properties at the aggregate level that significantly differs from those of corresponding single-molecule species, leading to a number of novel conceptual materials with state-dependent functionality. For developing such materials, new molecular scaffolds that allow modulating the structural and functional properties of aggregates in a controlled manner could be extremely helpful. In this study, we report a class of spiro-fused bicyclo[3,2,2] octatriene triptycene derivatives with a unique 3D molecular scaffolding structure that displays aggregation-induced emission (AIE) activity with bright solid-state blue luminescence. The core scaffold features a Y-shaped bicyclo[3,2,2]octatriene backbone and a vertical crossover arrangement of adjacent spiro-conjugated rings. Unlike classic bicyclo[2,2,2]octatrienes with high rigidity, this stereoscopic bicyclo[3,2,2]octatriene containing a seven-membered ring allows retaining certain flexibility in the molecular scaffold, which results in a weak fluorescence in dilute solutions (Φ F < 10%). However, the corresponding molecular aggregates emit intense fluorescence (Φ F = 50%-75%) and show prominent AIE activity because of the restriction of intramolecular scaffold motions. Moreover, in principle, these stereoscopic scaffold constructions with partially restricted flexibility facilitate the assembly of multiple different crystalline packing structures in both porous and nonporous forms depending on the growth conditions of crystalline aggregates. The obtained crystals with regular voids (12.85 × 6.89 Å each) show reversible luminescence in response to the adsorption/desorption of iodine vapor. These materials based on an unusual 3D scaffold exhibit a high degree of structural modulation at the aggregate level and demonstrate potential applications in chemical sensing and flexible optoelectronics, which may open up the exploration of highly stereoscopic molecular building blocks for developing functional aggregates.

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“…Synthetic difficulties, such as multistep preparations and/or moderate yields, limited the development of the homotriptycene chemistry. We published recently a simple route to homotriptycenes by an acid-catalyzed intramolecular electrophilic dehydration of 10,10-dibenzyl-9,10-dihydroanthrancen-9-ols . A high electron density in the benzyl groups proved to be the key factor for the desired transannular ring closure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Heterocyclic Homotriptycenes

Zhang

Cao²,

Liu³

et al. 2011

J. Org. Chem.

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A series of novel heterocyclic homotriptycenes bearing furan, thiophene, and pyridine rings, 7a-f, were synthesized by intramolecular dehydration reactions of 10,10-dihetarylmethyl-9,10-dihydroanthracen-9-ols 6a-f. In the presence of acids, the secondary alcohols 6a-f show different reactions which depend on the electron densities of the attached heterocyclic rings. The initially formed carbenium ions react in an electrophilic substitution with electron-rich heterocycles. The formation of a transannular bridge (1,7-elimination) leads to homotriptycenes in high yields. When the heterocyclic ring has a moderate electron density, two competitive reactions exist, which afford 9-monosubstituted anthracenes by 1,4-elimination or 9,10-disubstituted anthracenes by a rearrangement, respectively. Electron-deficient heterocycles undergo a disproportionation to give hydrocarbons and ketones.

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Synthesis of Fréchet-type dendritic homotriptycenes

Cited by 4 publications

References 44 publications

Radiochemistry

Radiochemistry

Spiro-fused bicyclo[3,2,2] octatriene-cored triptycene: synthesis, molecular packing, and functional aggregates

Synthesis of Heterocyclic Homotriptycenes

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