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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Published on: April 1, 2013

Conducting nanofibres of solvatofluorochromic cyclohexanetrione-dithiolylidene-based C₃ symmetric molecule

Kilingaru I Shivakumar¹, Goudappagouda¹, Rajesh G Gonnade²

¹Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune, 411008, India. sb.sukumaran@ncl.res.in gj.sanjayan@ncl.res.in and Academy of Scientific and Innovation Research, CSIR-National Chemical Laboratory, Pune, 411008, India.

Chemical Communications (Cambridge, England)

|December 13, 2017

Abstract:

We report a novel set of easily tailorable C₃ symmetric molecules with a π-extended core and adorned with different thioalkyl groups, exhibiting solvatofluorochromic and amphoteric redox behaviour. The nearly planar core exhibits intermolecular face-to-face π-stacking, SS and intramolecular SO interactions. Current-sensing atomic force microscopy studies revealed a high conductivity of ∼0.15 mS cm^-1 in the undoped J-aggregate nanofibres of the thiopropyl appended gelator.

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...

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