169616-16-4Relevant academic research and scientific papers
3,4-Dialkoxypyrrole for the Formation of Bioinspired Rose Petal-like Substrates with High Water Adhesion
Mortier, Claudio,Darmanin, Thierry,Guittard, Frédéric
, p. 12476 - 12487 (2016/12/07)
Self-organization is commonly present in nature and can lead to the formation of surface structures with different wettabilities. Indeed, in nature superhydrophobic (low water adhesion) and parahydrophobic (high water adhesion) properties exist, such as in lotus leaves and red roses, respectively. The aim of this work is to prepare parahydrophobic properties by electrodeposition. For this, pyrrole derivatives with two alkoxy groups of various lengths (from 1 to 12) were synthesized in 8 steps by adapting a method developed by Merz et al. We show that the alkyl chain length has a huge influence on the polymer solubility and as a consequence on the surface morphology and hydrophobicity. Moreover, the alkyl chain length should be at least greater than eight carbons in order to obtain parahydrophobic properties. The properties are also controlled by the electrolyte nature. These materials can be used for many potential applications in water harvesting and transportation and separation membranes.
3,4-Dialkoxypyrroles and 2,3,7,8,12,13,17,18-octaalkoxyporphyrins
Merz,Schropp,Dotterl
, p. 795 - 800 (2007/10/02)
A five-step general synthesis of 3,4-dialkoxypyrroles 7c-f is described starting with the condensation of dimethyl N-benzyliminodiacetate (1 b) and diethyl oxalate to give dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (2b), which is bis-O-alkylated to the corresponding 3,4-diethers 3c-g. Pyrrole N-benzyl cleavage followed by ester hydrolysis and decarboxylation leads to 7c-f in 10-50% overall yield. Pyrroles 7c-f react with formaldehyde or benzaldehydes to give meso-H- (8a-d) or meso-tetraaryloctaalkoxyporphyrins 9a-g in moderate yields.
