Follow up from Prof. Helena Dodziuk on ‘Excessive Science’

New or Old 2 – Nanoputians

A few weeks ago Prof. Helena Dodziuk wrote a guest post on ‘Excessive Science,’ and the issues this creates.  This guest post can be viewed here.  As a follow up on this matter, Prof. Helena Dodziuk has written a second guest post again on ‘New or Old,’ specifically this time on nanoputians.

Do you like Prof. Helena Dodziuk find similar occurrences in your areas of research? Let us know your thoughts on the conflicts of ‘New or Old’ research by leaving a comment at the bottom of this page.

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                                                                                     nanokid

Nanoputians1      

I have been always fascinated by molecules with unusual spatial structure2,3: the ones containing inverted 24 or planar 33,5,6 carbon atoms, planar 47 or unusually puckered 58 cyclohexane rings and other molecular “pathologies”. To name but a very few additional ones, olympiadane 69, knot 710, and endohedral fullerene complexes like 811 may be mentioned. They are fascinating, obtaining them presented a challenge but, as a rule, no applications were in sight when their syntheses were attempted. Cubane 9 is a good example: Eaton et al. published its synthesis in1964 without any hint to the applications, the researchers simply wanted to obtain this beautiful, highly symmetrical, and difficult to synthesize molecule. Much later we have learned that for ca 30 years polynitration of cubane was studied by US Army in the hope to get octanitrated cubane 1012 or that it could be used as HIV drug13.

I’ll write more about such unusual molecules later but here I would like to present for pure fun a synthetic paper on nanoputians, including nanokid 1 shown above, nanoballetdancers, and nanoputian chain forming a monolayer on a support.

   Olympiadane

endoheral fullerence complex

Chanteau and Tour1 synthesized what they call anthropomorphic molecules 11 – 14 (and some other, for instance nanoputians dancing in pairs) not because they wanted to use them for any application. They made it for fun! Running 11 and dancing 12 individual nanoputians and a group 13 as well as another group 14 forming a layer put on a support using thiol links. With the syntheses and compounds identification meticulously described it is an example of very good craftmanship. Carried out by sheer curiosity, earlier in French one called it “acte gratuit”.

nanokid

The next submission will be about 3D printing. It is a very interesting technique promising to revolutionize not only industry but also the whole everyday life.

(1) Chanteau, S. H., Tour, J. M. J. Org. Chem. 2003, 68, 8750-8766.
(2) Strained Hydrocarbons. Beyond van’t Hoff and Le Bel Hypothesis. With Foreword by Roald Hoffmann; Dodziuk, H., Ed., Ed.; Wiley-VCH: Weinheim, 2009.
(3) Dodziuk, H. In Modern Conformational Analysis. Elucidating Novel Exciting Molecular Structures; Wiley-VCH: Weinheim, 1995; pp 157-211.
(4) Wiberg, K. B. Chem. Rev. 1989, 89, 975.
(5) Hoffmann, R., Alder, R., Wilcox, J., C. F., J. Am. Chem. Soc. 1970, 92, 4992.
(6) Hoffmann, R., Alder, R. W., Wilcox, C. F. J. Am. Chem. Soc. 1979, 92, 4992.
(7) Dodziuk, H., Ostrowski, M. Eur. J. Org. Chem. 2006, 5231.
(8) Dodziuk, H., Nowinski, K. Bull. Pol. Acad. Sci., Chem. 1987, 35, 195.
(9) Amabilino, D. B., Ashton, P. R., Reder, A. S., Spencer, N., Stoddart, J. F. Angew. Chem, Int. Ed. Engl. 1994, 33, 1286.
(10) Dietrich-Buchecker, C.-O., Sauvage, J.-P. Angew. Chem. Int. Ed. 1989, 28, 189-192.
(11) Dodziuk, H. J. Nanosci. Nanotechnol. 2007, 7, 1102-1110.
(12) http://en.wikipedia.org/wiki/Octanitrocubane Octanitrocubane.
(13) http://www.chm.bris.ac.uk/webprojects2004/hook/applications/#Pharmaceuticals Applications of cubane: Pharmaceuticals; 2004.

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