The effects of noncovalent interactions on surface structures formed by diketopyrrolopyrrole pigment and its alkyl-derivatives on HOPG substrate

Akinori Honda, Yoshinori Tamaki, Kazuo Miyamura

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Abstract

Two-dimensional self-assembled structures formed by diketopyrrolopyrrole Pigment Red 254 (3,6-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) and its alkyl-derivatives at the liquid-HOPG interface were investigated by scanning tunneling microscope (STM). Pigment Red 254 is found to form two different surface structures (crystal-like structure and solvated crystal-like structure). Furthermore, in order to investigate the effect of hydrogen bonding, alkyl-derivatized Pigment Red 254 (PR-2Cn, n: alkyl chain length) were synthesized, and their self-assembled structures were analyzed. We found that surface structures of PR-2Cn varied depending on the intermolecular and molecule?substrate van der Waals interactions arising from the n-alkyl chains introduced instead of hydrogen bonding. Shorter alkyl chains of PR-2C10 resulted in the formation of multi domains. On the other hand, PR-2C12, PR-2C14, and PR-2C16 molecules that have longer alkyl chains formed stable single domain structures.

Original languageEnglish
Pages (from-to)969-975
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume88
Issue number7
DOIs
Publication statusPublished - 1 Jan 2015

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