Diazocine chemistry. VI. Aromaticity of 5,6-dihydrodibenzo[b,f][1,2]diazocine

Paudler, William W.; Zeiler, Andrew G.

doi:10.1021/jo01263a004

Cited by 43 publications

(24 citation statements)

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“…Intramolecular reductive coupling of the nitro groups to form the azo unit proceeds with notoriously low yields. The most frequently used procedure using Zn as the reducing agent in Ba(OH) 2 [12] or NaOH [13] gives irreproducible and low yields varying from 2% to not more than 19%. Glucose, however, in basic ethanolic solution turned out to furnish the azo compound 4 reproducibly in more than 20% yield.…”

Section: Resultsmentioning

confidence: 99%

Amino-substituted diazocines as pincer-type photochromic switches

Sell¹,

Näther²,

Herges³

2013

Beilstein J. Org. Chem.

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SummaryAzobenzenes are robust, reliable, and easy to synthesize photochromic switches. However, their high conformational flexibility is a disadvantage in machine-like applications. The almost free rotation of the phenyl groups can be restricted by bridging two ortho positions with a CH2CH2 group, as realized in the dihydrodibenzo diazocine framework. We present the synthesis and properties of 3,3’-amino- and 3,3’-acetamido substituted diazocines. Upon irradiation with light of 405 and 530 nm they isomerize from the cis to the trans configuration and back, and thereby perform a pincer-like motion. In the thermodynamically more stable cis isomer the lone pairs of the amino nitrogen atoms point towards each other, and in the trans form they point in opposite directions. The distance between the amino nitrogen atoms changes between 8 Å (cis) and 11 Å (trans isomer).

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Section: Resultsmentioning

confidence: 99%

Amino-substituted diazocines as pincer-type photochromic switches

Sell¹,

Näther²,

Herges³

2013

Beilstein J. Org. Chem.

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“…This compound was acetylated (to give 6 ) and then nitrated to give 1,2‐bis(2‐nitro‐5‐acetamidophenyl)ethane ( 5 ). A two‐step oxidation protocol, adapted from that of Paudler and Zeiler,11 using Ba(OH) 2 , Zn, and HgO led to para ‐diacetamido‐substituted C 2 ‐bridged azobenzene 2 . Hydrolysis of the two acetamido groups of 2 with KOH resulted in para ‐diamino‐substituted C 2 ‐bridged azobenzene 4 , which was treated with chloroacetic anhydride/pyridine to give para ‐di(α‐chloroacetamido)‐substituted C 2 ‐bridged azobenzene 3 .…”

Section: Methodsmentioning

confidence: 99%

Bidirectional Photocontrol of Peptide Conformation with a Bridged Azobenzene Derivative

et al. 2012

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It goes both ways: A thiol-reactive cross-linker based on a bridged azobenzene derivative permits photoreversible control of peptide conformation on irradiation with violet (407 nm) and green (500-550 nm) light (see picture) through isomerization of the cross-linker. The large separation of the absorbance bands of the cis (yellow) and trans (red) isomers enables complete bidirectional photoswitching.

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“…The photo-switchable molecule 5,6-dihydrodibenzo[c,g][1,2]diazocine (1) was synthesized according to published procedures. 42,43 For in situ sample irradiation, light emitted from high power LEDs (lumitronix) was directly coupled into the blunt and polished end of a 4 mm thick optical fiber (ceramoptec). At the tip of the fiber, the nylon jacket was removed and a pencil…”

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confidence: 99%