Synthesis of Functionalized Molecular Motors

Abstract

Synthetic routes to two molecular motors are reported. The sterically hindered central olefinic bond connecting the two halves of these C ₂-symmetric molecules was prepared by a McMurry reaction. In this way, a motor with two five-membered rings and a motor with two six-membered rings were prepared, both with two versatile methoxy substituents at positions not interfering with the rotary behavior.

alkenes - arenes - nanostructures - McMurry reactions

References

<A NAME="RT12204SS-1">1</A> Peercy PS. Nature (London, UK)  2000,  406:  1023 

<A NAME="RT12204SS-2A">2a</A> Balzani V. Credi A. Raymo FM. Stoddart JF. Angew. Chem. Int. Ed.  2000,  39:  3348 

<A NAME="RT12204SS-2B">2b</A> Feringa BL. Koumura N. van Delden RA. ter Wiel MKJ. Appl. Phys. A: Mater. Sci. Process  2002,  75:  301 

<A NAME="RT12204SS-3">3</A> Kelly TR. De Silva H. Silva RA. Nature (London, UK)  1999,  401:  150 

<A NAME="RT12204SS-4">4</A> Jiménez MC. Dietrich-Buchecker C. Sauvage J.-P. Angew. Chem. Int. Ed.  2000,  39:  3284 

<A NAME="RT12204SS-5">5</A> Badjic JD. Balzani V. Credi A. Silvi S. Stoddart JF. Science  2004,  303:  1845 

<A NAME="RT12204SS-6">6</A> Muraoka T. Kinbara K. Kobayashi Y. Aida T. J. Am. Chem. Soc.  2003,  125:  5612 

<A NAME="RT12204SS-7">7</A> Thordarson P. Bijsterveld EJA. Rowan AE. Nolte RJM. Nature (London, UK)  2003,  424:  915 

<A NAME="RT12204SS-8">8</A> Koumura N. Zijlstra RWJ. van Delden RA. Feringa BL. Nature (London, UK)  1999,  401:  152 

<A NAME="RT12204SS-9A">9a</A> Koumura N. Geertsema EM. Meetsma A. Feringa BL. J. Am. Chem. Soc.  2000,  122:  12005 

<A NAME="RT12204SS-9B">9b</A> Koumura N. Geertsema EM. van Gelder MB. Meetsma A. Feringa BL. J. Am. Chem. Soc.  2002,  124:  5037 

<A NAME="RT12204SS-10">10</A> ter Wiel MKJ. Delden RA. van Meetsma A. Feringa BL. J. Am. Chem. Soc.  2003,  125:  15076 

<A NAME="RT12204SS-11">11</A> Flood AH. Ramirez RJA. Deng WQ. Muller RP. Goddard WA. Stoddart JF. Aust. J. Chem.  2004,  57:  301 

<A NAME="RT12204SS-12">12</A>

ter Wiel, M. K. J.; van Delden, R. A.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc., submitted.

<A NAME="RT12204SS-13A">13a</A> Short WF. Stromberg H. Wiles AE. J. Chem. Soc.  1936,  319 

<A NAME="RT12204SS-13B">13b</A> Bachmann WE. Horton WJ. J. Am. Chem. Soc.  1947,  69:  58 

<A NAME="RT12204SS-14">14</A> Ghosal M. J. Org. Chem.  1960,  25:  1856 

<A NAME="RT12204SS-15">15</A>

This work is in progress.

<A NAME="RT12204SS-16A">16a</A> Gerlach H. Wetter H. Helv. Chim. Acta  1974,  57:  2306 

<A NAME="RT12204SS-16B">16b</A> Hoover HW. McCall MA. Dickey JB. J. Am. Chem. Soc.  1957,  79:  1963 

<A NAME="RT12204SS-17">17</A> Harvey RG. Cortez C. Sawyer TW. DiGiovanni J. J. Med. Chem.  1988,  31:  1308 

<A NAME="RT12204SS-18">18</A> Kemperman GJ. Roeters TA. Wilberink PW. Eur. J. Org. Chem.  2003,  1681 

<A NAME="RT12204SS-19">19</A> Wrobel J. Dietrich A. Gorham BJ. Sestanj K. J. Org. Chem.  1990,  55:  2694 

<A NAME="RT12204SS-20">20</A> Koelsch CF. Org. Synth.  1940,  20:  18 

<A NAME="RT12204SS-21">21</A> Franzen H. Stäuble G. J. Prakt. Chem.  1921,  103:  352