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Synlett 2013; 24(19): 2545-2549
DOI: 10.1055/s-0033-1339882
DOI: 10.1055/s-0033-1339882
letter
Towards a Perylene-Containing Nanohoop
Further Information
Publication History
Received: 04 August 2013
Accepted after revision: 03 September 2013
Publication Date:
28 October 2013 (online)
![](https://www.thieme-connect.de/media/synlett/201319/lookinside/thumbnails/10.1055-s-0033-1339882-1.jpg)
Abstract
We report the synthesis of a belt-shaped macrocycle, herein referred to as a nanohoop, that contains binaphthyl moieties separated by phenyl groups.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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- 12 A 7 mL microwave vial containing a magnetic stirring bar was flame-dried under vacuum and back-filled with argon after cooling to room temperature. To this vial was added 4 (18.2 mg, 10 μmol), TsOH·H2O (30.4 mg, 0.16 mmol), and anhydrous toluene (3.00 mL). The vial was then sealed and heated in a CEM Discover Microwave, stirring at 150 °C for 60 min. After the reaction mixture was cooled to room temperature, dichloromethane was added and the organic layer was washed with 1 M aq NaOH (× 3). The organic and aqueous layers were then separated prior to washing the organic layer with brine. The cumulative organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was subjected to column chromatography (CH2Cl2–hexane, 20:80) to afford 1 (4.9 mg, 38%) as an off-white, slightly yellow solid. 1H NMR (500 MHz, DMSO-d6, 150 °C): δ = 8.13 (1 H), 8.02 (2 H), 7.77 (1 H), 7.71 (3 H), 7.56 (5 H), 7.43 (2 H). MADLI-TOF MS: m/z calcd for C102H70: 1306.55; found: 1306.84.