Title: Complex Structures Resulting from Carboxylic Acid Self-Assembly: Comparison of 2-Naphthoic Acid to Quinaldic Acid and 3-Quinoline Carboxylic Acid
Abstract: Scanning tunneling microscopy was used to study the self-assembly of three molecules on the Au(111) surface: 2-naphthoic acid, quinaldic acid, and 3-quinoline carboxylic acid. All three compounds consist of two fused six-membered rings functionalized at the same position with a carboxylic acid group. Despite their chemical similarity, widely different structures were observed to result from self-assembly after pulse deposition. 2-Naphthoic acid forms cyclically hydrogen-bonded pentamers, a metastable structure that transitions to rows of dimers upon gentle annealing. Quinaldic acid and 3-quinoline carboxylic acid form dimers, tetramers, and hexamers, but no pentamers. Differences in self-assembly between these three compounds are attributed to the ability of quinaldic acid and 3-quinoline carboxylic acid to form zwitterionic species.
Publication Year: 2019
Publication Date: 2019-01-01
Language: en
Type: article
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