Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly.
Multichromophoric hydrogen-bonded assemblies 1(3) small middle dot(BAR)(6) are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV/visible (Vis) absorption maximum (Delta lambda(max) = 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10(-4) M). The determined C(50%) values of 2-3 microM in benzene show the extremely high stability of these hydrogen-bonded assemblies.
Prins
L J
LJ
Laboratory of Supramolecular Chemistry and Technology, MESA(+) Research Institute, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.
Thalacker
C
C
Würthner
F
F
Timmerman
P
P
Reinhoudt
D N
DN
D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010860:Pigments, Biological / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D046911:Macromolecular Substances; D010860:Pigments, Biological; D011744:Pyrimidinones; C003954:merocyanine dye