A Porphyrin Fused to Four Anthracenes

Davis, Nicola K. S.; Thompson, Amber L.; Anderson, Harry L.

doi:10.1021/ja109671f

Cited by 229 publications

(130 citation statements)

References 18 publications

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“…A new strategy of acid-catalysed reactions of indole methanols with a 3-aryl-4,6-dimethoxyindole-7-aldehyde leads to an efficient synthesis of a calix [3]indole with 2,2; 7,2; 7,7-links. A new calix [4]indole containing four indole units with 2,2; 7,2; 7,7; 2,7-links has also been prepared by this strategy.…”

Section: Introductionmentioning

confidence: 99%

“…

Key words: indoles, diindolylmethanes, macrocyclic compounds, acid-catalysed reactions, ipso-substitution reactions, formaldehyde extrusion Macrocycles containing pyrroles are well established in the field of supramolecular chemistry for the reason that the pyrrole NH groups readily form hydrogen bonds with guest molecules or on deprotonation the nitrogen atoms can bind to metal ions.

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Two well-known systems are calix[4]pyrroles and porphyrins.

…”

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confidence: 99%

“…The synthesis of 3-substituted 4,6-dimethoxyindoles has enabled their enhanced activity at C2 and C7 to be investigated in a variety of ways. [6][7][8][9][10][11] Acid-catalysed reactions of these indoles with aryl aldehydes have led to the formation of calix [3]indoles, presumably via intermediate indole methanols. …”

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confidence: 99%

“…[1][2][3] Two well-known systems are calix [4]pyrroles and porphyrins. 4,5 However macrocycles containing indoles have not been widely studied in this context, despite the similar acidity of an indole NH group to that of a pyrrole.…”

mentioning

confidence: 99%

“…In principle, these calix [3]indoles can contain either three arylmethylene linkages between C2 and C7, or one such linkage between C2 and C2, C2 and C7, and C7 and C7 (see Figure 1). Both types have already been synthesised.…”

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confidence: 99%

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A New Strategy for Calixindole Formation: Synthesis of a Calix[3]indole with 2,2; 7,2; 7,7-Methylene Linkages and a New Calix[4]indole with 2,2; 7,2; 7,7; 2,7-Methylene Linkages

Somphol

Chen

Bhadbhade

et al. 2012

Synlett

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Abstract:A new strategy of acid-catalysed reactions of indole methanols with a 3-aryl-4,6-dimethoxyindole-7-aldehyde leads to an efficient synthesis of a calix [3]indole with 2,2; 7,2; 7,7-links. A new calix [4]indole containing four indole units with 2,2; 7,2; 7,7; 2,7-links has also been prepared by this strategy.Key words: indoles, diindolylmethanes, macrocyclic compounds, acid-catalysed reactions, ipso-substitution reactions, formaldehyde extrusion Macrocycles containing pyrroles are well established in the field of supramolecular chemistry for the reason that the pyrrole NH groups readily form hydrogen bonds with guest molecules or on deprotonation the nitrogen atoms can bind to metal ions. 1-3Two well-known systems are calix[4]pyrroles and porphyrins. 4,5 However macrocycles containing indoles have not been widely studied in this context, despite the similar acidity of an indole NH group to that of a pyrrole. The expansion of the five-membered pyrrole ring system to the larger and more highly conjugated indole system creates new synthetic and structural possibilities with great potential for supramolecular chemistry. The synthesis of 3-substituted 4,6-dimethoxyindoles has enabled their enhanced activity at C2 and C7 to be investigated in a variety of ways. [6][7][8][9][10][11] Acid-catalysed reactions of these indoles with aryl aldehydes have led to the formation of calix [3]indoles, presumably via intermediate indole methanols. 12In principle, these calix[3]indoles can contain either three arylmethylene linkages between C2 and C7, or one such linkage between C2 and C2, C2 and C7, and C7 and C7 (see Figure 1). Both types have already been synthesised. Both 3-substituted 4,6-dimethoxyindole-7-carbaldehydes and 4,6-dimethoxyindole-2-carbaldehydes can be prepared via the Vilsmeier-Haack formylation reaction. 13Subsequent reduction of the formyl groups with sodium borohydride affords the simple indole C7-and C2-methanols, which can also undergo acid-catalysed cyclisation to calix[3]indoles. [14][15][16][17] However, in this process, calix[4]indoles can also be generated, and show four methylene linkages between C2 and C7. There are four possible ways of linking four indoles through the C2 and C7 positions with four methylene links. These basic structures are shown in Figure 2. We now report new, highly effective stepwise sequences for the synthesis of a calix [3]indole and the first example of a calix[4]indole with a 2,2; 7,2; 7,7; 2,7 set of methylene linkages. These stepwise sequences involve the monoindole 2,7-dimethanol 1 and the diindolyl 7,7′-dimethanol 2, which have been previously reported. 1 with two equivalents of the indole-7-aldehyde 3 in isopropanol containing p-toluenesulfonic acid gave the triindolyldimethane dialdehyde 4, 18 which precipitated from the reaction mixture and was obtained in 90% yield. Reduction of the dialdehyde 4 with sodium borohydride in a mixture of ethanol and tetrahydrofuran gave the dimethanol 5 in 98% yield. Treatment of this dimethanol 5 with p-toluenesulfonic acid in...

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Section: Introductionmentioning

confidence: 99%

“…

1-3

Two well-known systems are calix[4]pyrroles and porphyrins.

…”

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confidence: 99%

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confidence: 99%

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confidence: 99%

mentioning

confidence: 99%

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A New Strategy for Calixindole Formation: Synthesis of a Calix[3]indole with 2,2; 7,2; 7,7-Methylene Linkages and a New Calix[4]indole with 2,2; 7,2; 7,7; 2,7-Methylene Linkages

Somphol

Chen

Bhadbhade

et al. 2012

Synlett

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Organic Synthesis and Reactivity of Porphyrins

Senge¹,

Meindl²

2022

Fundamentals of Porphyrin Chemistry

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Highly Efficient Rubrene–Graphene Charge‐Transfer Interfaces as Phototransistors in the Visible Regime

et al. 2017

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Atomically thin materials such as graphene are uniquely responsive to charge transfer from adjacent materials, making them ideal charge-transport layers in phototransistor devices. Effective implementation of organic semiconductors as a photoactive layer would open up a multitude of applications in biomimetic circuitry and ultra-broadband imaging but polycrystalline and amorphous thin films have shown inferior performance compared to inorganic semiconductors. Here, the long-range order in rubrene single crystals is utilized to engineer organic-semiconductor-graphene phototransistors surpassing previously reported photogating efficiencies by one order of magnitude. Phototransistors based upon these interfaces are spectrally selective to visible wavelengths and, through photoconductive gain mechanisms, achieve responsivity as large as 10 A W and a detectivity of 9 × 10 Jones at room temperature. These findings point toward implementing low-cost, flexible materials for amplified imaging at ultralow light levels.

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A Porphyrin Fused to Four Anthracenes

Cited by 229 publications

References 18 publications

A New Strategy for Calixindole Formation: Synthesis of a Calix[3]indole with 2,2; 7,2; 7,7-Methylene Linkages and a New Calix[4]indole with 2,2; 7,2; 7,7; 2,7-Methylene Linkages

A New Strategy for Calixindole Formation: Synthesis of a Calix[3]indole with 2,2; 7,2; 7,7-Methylene Linkages and a New Calix[4]indole with 2,2; 7,2; 7,7; 2,7-Methylene Linkages

Organic Synthesis and Reactivity of Porphyrins

Highly Efficient Rubrene–Graphene Charge‐Transfer Interfaces as Phototransistors in the Visible Regime

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