Synthesis and self-association of dibenzothiophene derivatives for simulation of hydrogen bonding interaction in asphaltenes

Abstract

The dibenzothiophene derivatives, namely 2-(dibenzothiophene-2-carbonyl)benzoic acid and 2-(dibenzothiophene-2-carbonyl)alkyl benzoate, were synthesized and characterized by nuclear magnetic resonance ( 1 H NMR), matrix-assisted laser desorption/ionization time of flight mass spectrometry, and elemental analysis. The selfassociation behavior of these dibenzothiophene derivatives in CH 2 Cl 2 and CH 3 CN was investigated using UV-visible absorption spectroscopy, fourier transform infrared spectroscopy, and atomic force microscopy. It was found that the carboxylic acid exhibited a strong self-association trend in CH 2 Cl 2 solution at a concentration of about 5 9 10 -7 M. Hydrogen bonding of carboxyl in the dibenzothiophene derivatives was confirmed to be the main driving force for the formation of the carboxylic acid aggregates.