Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution

Schaefer C, Rozhenko AB, Mattay J (2009)
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 8(8): 1187-1194.

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Abstract
Several resorcin[4]arenes functionalized with two anthracene units on opposite sides of the upper rim of the macrocycle were synthesized. We investigated the potentially photochromic properties of these systems, with the main focus on the intramolecular [4+4] cycloaddition of the anthracenes and its reversibility by thermal ring opening. Whereas compound 9 proved to be a switchable host system (by irradiation and temperature, T-type photochromic substances), compounds 10-12 formed intramolecular photodimers upon irradiation, which are only stable at low temperature. The reopening occurred immediately at room temperature and was followed by UV/VIS spectroscopy. Further investigations showed that the cyclodimer of 11 can be stabilized significantly by sodium cations due to crown ether-like complexation. Additionally, quantum chemical calculations were performed to evaluate the different behaviour.
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Schaefer C, Rozhenko AB, Mattay J. Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. 2009;8(8):1187-1194.
Schaefer, C., Rozhenko, A. B., & Mattay, J. (2009). Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 8(8), 1187-1194.
Schaefer, C., Rozhenko, A. B., and Mattay, J. (2009). Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 8, 1187-1194.
Schaefer, C., Rozhenko, A.B., & Mattay, J., 2009. Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 8(8), p 1187-1194.
C. Schaefer, A.B. Rozhenko, and J. Mattay, “Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution”, PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, vol. 8, 2009, pp. 1187-1194.
Schaefer, C., Rozhenko, A.B., Mattay, J.: Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. 8, 1187-1194 (2009).
Schaefer, Christian, Rozhenko, Alexander B., and Mattay, Jochen. “Photochromic resorcin[4]arenes: stabilization of intramolecular anthracene dimers in solution”. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 8.8 (2009): 1187-1194.
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3 Citations in Europe PMC

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Reversible photochemically gated transformation of a hemicarcerand to a carcerand.
Wang H, Liu F, Helgeson RC, Houk KN., Angew. Chem. Int. Ed. Engl. 52(2), 2013
PMID: 23172821
Anthracene-resorcin[4]arene-based capsules: synthesis and photoswitchable features.
Bringmann S, Brodbeck R, Hartmann R, Schafer C, Mattay J., Org. Biomol. Chem. 9(21), 2011
PMID: 21927749

28 References

Data provided by Europe PubMed Central.

Reverse engineering of an affinity-switchable molecular interaction characterized by atomic force microscopy single-molecule force spectroscopy.
Anselmetti D, Bartels FW, Becker A, Decker B, Eckel R, McIntosh M, Mattay J, Plattner P, Ros R, Schafer C, Sewald N., Langmuir 24(4), 2008
PMID: 18062710
Kemp's triacid attached to octa-O-methyl resorc[4]arenes: conformations in solution and comparative binding studies with various 2-amino pyridines
Stoll, Tetrahedron 64(17), 2008
A kinetic study of guest displacement reactions on a host-guest complex with a photoswitchable calixarene.
Letzel MC, Schafer C, Novara FR, Speranza M, Rozhenko AB, Schoeller WW, Mattay J., J Mass Spectrom 43(11), 2008
PMID: 18698554

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