Photocyclizable resorcin[4]arene dimers

The synthesis of covalently linked dimers, containing two resorcin[4]arene moieties connected over two 9,10-functionalized anthracene units, is reported. Besides the synthetic route, which involves for example the formation of anthracene-9,10-dialkanols ( and ), and characterization of the compounds, the photochemical properties, introduced through the anthracene groups, were investigated by means of UV/VIS spectroscopy. Both resorcin[4]arene dimers ( and ) were able to undergo an intramolecular [4+4] cycloaddition, therefore changing the size of the inner cavity. Unfortunately, the back reaction, which was expected to take place on irradiation below 300 nm or upon heating, was not observed yet and will be the focus of our future work.

[1]  A. Becker,et al.  Reverse engineering of an affinity-switchable molecular interaction characterized by atomic force microscopy single-molecule force spectroscopy. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[2]  D. Anselmetti,et al.  Photochemical single-molecule affinity switch. , 2007, Journal of the American Chemical Society.

[3]  D. Anselmetti,et al.  On the way to supramolecular photochemistry at the single-molecule level , 2006 .

[4]  J. Mattay,et al.  Preparation of photocyclizable dianthracene derivatives of resorc[4]arenes which are potential photoswitches. , 2004, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[5]  A. Castellan,et al.  Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage , 2001 .

[6]  A. Castellan,et al.  Photodimerization of anthracenes in fluid solution:structural aspects , 2000 .

[7]  J. Sherman,et al.  Carceplexes and Hemicarceplexes. , 1999, Chemical reviews.

[8]  H. Whitlock,et al.  A Synthetic Receptor Which Uses Multiple Edge-Face Interactions To Bind Aromatic Guests. , 1998, The Journal of organic chemistry.

[9]  M. Winnik,et al.  Fluorescence energy transfer studies in a cross-linked polyurethane network , 1995 .

[10]  H. Becker.  Unimolecular photochemistry of anthracenes , 1993 .

[11]  D. Cram,et al.  The Taming of Cyclobutadiene , 1991 .

[12]  D. Cram,et al.  Constrictive binding of large guests by a hemicarcerand containing four portals , 1991 .

[13]  Young Hwan Kim,et al.  Host-guest complexation. 47. Carcerands and carcaplexes, the first closed molecular container compounds , 1988 .

[14]  Young Hwan Kim,et al.  Shell closure of two cavitands forms carcerand complexes with components of the medium as permanent guests , 1985 .

[15]  M. Miller,et al.  Some meso-Substituted Anthracenes. I. 9,10-Bis-(chloromethyl)-anthracene as a Synthetic Intermediate1 , 1955 .

[16]  G. Badger.  93. The synthesis of growth-inhibitory polycyclic compounds. Part III , 1939 .