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Photomodulation of Two-Dimensional Self-Assembly of Azobenzene-Hexa- peri-hexabenzocoronene-Azobenzene Triads

Hou, I. C.-Y.; Diez-Cabanes, V.; Galanti, A.; Valášek, Michal; Mayor, Marcel; Cornil, J.; Narita, A.; Samorì, P.; Müllen, K.

Abstract:
Achieving exquisite control over self-assembly of functional polycyclic aromatic hydrocarbons (PAH) and nanographene (NG) is essential for their exploitation as active elements in (nano)technological applications. In the framework of our effort to leverage their functional complexity, we designed and synthesized two hexa-peri-hexabenzocoronene (HBC) triads, pAHA and oAHA, decorated with two light-responsive azobenzene moieties at the pseudo-para and ortho positions, respectively. Their photoisomerization in solution is demonstrated by UV–vis absorption. 1H NMR measurements of oAHA suggested 23% of Z-form can be obtained at a photostationary state with UV irradiation (366 nm). Scanning tunneling microscopy imaging revealed that the self-assembly of pAHA and oAHA at the solid–liquid interface between highly oriented pyrolytic graphite (HOPG) and their solution in 1,2,4-trichlorobenzene can be modulated upon light irradiation. This is in contrast to our previous work using HBC bearing a single azobenzene moiety, which did not show such photomodulation of the self-assembled structure. Upon E-Z isomerization both pAHA and oAHA displayed an increased packing density on the surface of graphite. ... mehr

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Verlagsausgabe §
DOI: 10.5445/IR/1000096683
Veröffentlicht am 01.10.2019
Coverbild
Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Publikationstyp Zeitschriftenaufsatz
Jahr 2019
Sprache Englisch
Identifikator ISSN: 0897-4756, 1520-5002
KITopen-ID: 1000096683
HGF-Programm 43.21.04 (POF III, LK 01)
Erschienen in Chemistry of materials
Band 31
Heft 17
Seiten 6979-6985
Vorab online veröffentlicht am 12.06.2019
Nachgewiesen in Web of Science
Scopus
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