Positioned substituent effect on self-assembly behaviors of perylene diimide derivatives on graphite

Journal of Colloid and Interface Science
Qian WeiPeng Jiang

Abstract

Three kinds of π-conjugated perylenetetracarboxylic diimide (PTCDI)-based organic functional derivatives, i.e., N,N'-di(2-ethylhexyl)-3,4,9,10-perylene diimide (molecule 1), N,N'-di(2-ethylhexyl)-1,7-dithien-2-yl-3,4,9,10-perylene diimide (molecule 2), N,N'-di(2-ethylhexyl)-1,7-di(2-bromothien-5-yl)-perylene-3,4,9,10-perylene diimide (molecule 3), have been prepared and investigated by using a scanning tunneling microscopy under ambient conditions. All of them can form long-ranged ordered self-assembled monolayer (SAM) with two different phase structures on highly oriented pyrolitic graphite (HOPG) surface. Coexistence of the two phases in the formed SAMs depends strongly on cooperation of various interactions including the molecule-substrate and molecule-molecule. Orientation of the molecular perylene cores primarily governs the molecular orientation in the SAMs by π-π interaction of the molecule-substrate through uttermost matching the graphite surface lattice. At the same time, the branched alkyl-chain substituents at N-sites can adjust intermolecular distances through conformation change while cyclic π-conjugated substituents at bay-positions lead to molecular rotation movement on HOPG, driven by the decreased molecule-subs...Continue Reading

Citations

Apr 6, 2021·ACS Applied Materials & Interfaces·Yuchuan XiaoQingdao Zeng
Feb 28, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Renato BuzioAntonio Cassinese
Sep 22, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Lin MaQingdao Zeng

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