4,13-bis(2-(9-Anthryloxy)ethyl)-4,13-diazonia-[18]crown-6 bis(trifluoroacetate) monohydrate

Sample Originator: Michael B. Hursthouse, Simon J. Coles, J. -P. Desvergne, H. Bouas-Laurent, J. H. R. Tucker, G. McSkimming and Mark E. Light.

C₄₄H₅₂N₂O₆ . 2C₂F₃O . H₂O

InChI=1/2C22H26NO3.C2F4O2.C2F3O2.O/c1-23(11-13-25-16-15-24-2)12-14-26-22-20-9-5-3-7-18(20)17-19-8-4-6-10-21(19)22;1-2-24-15-16-25-13-11-23-12-14-26-22-20-9-5-3-7-18(20)17-19-8-4-6-10-21(19)22;3-2(1(7)8)4-6(2)5-2;3-2(4,5)1(6)7;/h2*3-10,17,23H,1-2,11-16H2;;;

Identification Number:	10.5258/ecrystals/92
Date Created:	14 June 1999
Deposited On:	21 Jan 2008 15:29
Deposited By:	A.N. Admin

Depositor Comments

Aza-crown ethers 2 and 3 with anthracene-containing pendant arms have been synthesised and characterised. Both compounds bind Group 1 metal cations in solution, forming complexes of 1:1 stoichiometry. The properties of compound 2 and its complexes have been studied by a range of techniques, including NMR, UV and fluorescence spectroscopy and X-ray crystallography. The pendant arms can adopt either a cis or a trans geometry, the cis geometry favoured with larger cations. The geometry of the complex affects the fluorescence properties of the system, with larger cations giving higher excimer/monomer ratios. Upon irradiation at >300 nm, coronand 2 forms the cryptand 5 through a reversible intramolecular [4+4] cycloaddition reaction. The rates of the forward and reverse reactions of this photochromic process are cation dependent; in particular the rate of the thermal reverse reaction is decreased by smaller cations and increased by larger cations, especially Rb+. The metal binding constants in methanol for 2 and 5 have been determined, revealing that the cryptand 5 binds Na+ and Rb+ more weakly than crown ether 2 by over two orders of magnitude.

Data collection parameters

Chemical formula	C48 H52 F6 N2 O11
Crystal morphology
Crystal system	Triclinic
Space group symbol	P-1
Cell length a	11.352(2)
Cell length b	12.894(3)
Cell length c	17.223(3)
Cell angle alpha	68.61(3)
Cell angle beta	83.13(3)
Cell angle gamma	80.13(3)
Data collection temperature	293(2)

Refinement results

Solution figure of merit	0.0547
R Factor (Obs)	0.0595
R Factor (All)	0.0884
Weighted R Factor (Obs)	0.1684
Weighted R Factor (All)	0.1843

Citation: Hursthouse, Michael B. and Coles, Simon J. and Desvergne, J. -P. and Bouas-Laurent, H. and Tucker, J. H. R. and McSkimming, G. and Light, Mark E. (1999) University of Southampton, Crystal Structure Report Archive. (doi:10.5258/ecrystals/92)
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