4,5-Pyrenocyanine--just another phthalocyanine? A STM and 2D WAXS study

Chemistry : a European Journal
Lukas ZöphelKlaus Müllen

Abstract

Pyrene-fused tetraazaporphyrins were synthesized from pyrene-4,5-dicarbonitrile precursors using a recently reported procedure as the key step for the asymmetric substitution of pyrene. Metal-free, zinc- and lead-centered pyrenocyanines were obtained and their optical properties as well as their molecular assembly in the solution and bulk phases and at the liquid/solid interface were studied. The characteristic Q-band appears broadened, most likely owing to distortion of the molecule introduced by the steric demand of the angularly extended aromatic residue. The angular annulation does not bathochromically shift the Q-band as far as would have been expected for the linear case. Peripheral substitution with linear and branched alkoxy chains affords solubility of the compounds in organic solvents. The influence of the distinct steric demand of the substituents on aggregation was investigated for metal-centered pyrenocyanines by using temperature-dependent (1)H NMR and UV/Vis spectroscopy. The self-assembly at the liquid/solid interface was studied using scanning tunneling microscopy. The alkoxy substituents facilitate the anchoring of these slightly non-planar molecules on the surface of graphite. Pyrenocyanine molecules form wel...Continue Reading

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Citations

Feb 3, 2015·Chemistry : a European Journal·Houhe PanJianzhuang Jiang
Sep 17, 2014·Chemistry : a European Journal·Marta Viciano-ChumillasFabien Silly
Jul 23, 2013·Chemistry, an Asian Journal·Kunal S MaliSteven De Feyter
Apr 14, 2015·Chemistry : a European Journal·Matthias Georg SchwabKlaus Müllen
Jul 9, 2013·Journal of the American Chemical Society·Jie ShuMichael Ryan Hansen

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