2018
DOI: 10.1002/ange.201809514
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Reversible Photoisomerization of Monolayers of π‐Expanded Oligothiophene Macrocycles at Solid–Liquid Interfaces

Abstract: Self-assembled monolayers of a p-expanded oligothiophene macrocycle undergo photoisomerization between their Z,Z and E,E diastereomers at the interface between octanoic acid solutions and highly oriented pyrolytic graphite (HOPG). The switching process proceeds in situ at the solidliquid interface and was followed by scanning tunneling microscopy( STM). Upon illumination with light at 365 nm (546 nm), amonolayer of Z,Z-8mer (E,E-8mer) photoisomerizes to the E,E-8mer (Z,Z-8mer) form with changes in 2D hexagonal… Show more

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Cited by 6 publications
(3 citation statements)
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References 42 publications
(54 reference statements)
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“…Formation of stable assemblies for different photoactive states without desorption/readsorption of molecules is essential for development of responsive surfaces and devices. 45,49,50 In our case, the packing density increased upon irradiation with UV light, and we did not monitor the presence of regions with fuzzy contrast between domains of different assemblies. It is therefore likely that the physisorbed molecules undergo a process that involves the subsequential desorption, isomerization in solution, and readsorption onto the surface where void space is created by the shrinking of the assemblies.…”
Section: Chemistry Of Materialsmentioning
confidence: 54%
“…Formation of stable assemblies for different photoactive states without desorption/readsorption of molecules is essential for development of responsive surfaces and devices. 45,49,50 In our case, the packing density increased upon irradiation with UV light, and we did not monitor the presence of regions with fuzzy contrast between domains of different assemblies. It is therefore likely that the physisorbed molecules undergo a process that involves the subsequential desorption, isomerization in solution, and readsorption onto the surface where void space is created by the shrinking of the assemblies.…”
Section: Chemistry Of Materialsmentioning
confidence: 54%
“…Introduction p-Conjugated macrocycles with well-dened diameters have received signicant attention in the last few decades, mainly because of their unique optical and electronic properties, their host-guest capabilities, and their potential as building blocks for supramolecular materials. [1][2][3][4][5][6] Many p-conjugated macrocyclic systems aggregate into columnar structures, 4,7-11 producing molecular channels that, with the appropriate inner-core functionalization, may give rise to ion channels, rod-like micellar aggregates, and even reaction chambers. [12][13][14][15] A particularly intriguing class of p-conjugated macrocycles is macrocyclic oligothiophenes (C-nT, Chart 1), introduced by Bäuerle's group in sizes ranging from C-8T to C-35T.…”
mentioning
confidence: 99%
“…In the course of our studies, we employed McMurry coupling for the synthesis of macrocyclic π-extended thiophene oligomers composed of thienylene–ethynylene and thienylene–vinylene units . Oligothiophene-containing π-conjugated macrocycles are redox-active molecules without the terminal unit, exhibiting attractive optoelectronic properties, and therefore, π-extended thiophene-containing macrocycles with continuous π-conjugation are promising candidates for multifunctional materials …”
Section: Introductionmentioning
confidence: 99%