Light-stimulated switching of azobenzene-containing self-assembled monolayers

Hamelmann, Frank; Heinzmann, Ulrich; Siemeling, Ulrich; Bretthauer, Frauke; Brüggen, Jens Vor der

doi:10.1016/j.apsusc.2003.08.006

Cited by 34 publications

(24 citation statements)

References 16 publications

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“…Reisomerization to the trans isomer occurs upon irradiation with blue light of 435 nm or by thermal relaxation. 5 Self-assembled adlayers of azobenzene-containing compounds on Au surfaces, in most cases basing on thiols, have been intensively studied. 2,3,6 We have introduced the so-called platform concept and implemented it using derivatives of the triazatriangulenium (TATA) ion (Fig.…”

Section: Introductionmentioning

confidence: 99%

X-ray spectroscopy characterization of azobenzene-functionalized triazatriangulenium adlayers on Au(111) surfaces

Ulrich

Jung

Strunskus

et al. 2015

Phys. Chem. Chem. Phys.

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Triazatriangulenium (TATA) platform molecules allow the preparation of functionalized surfaces with well-defined lateral spacings of freestanding functional groups. Using scanning tunneling microscopy, synchrotron-based X-ray photoelectron spectroscopy, near edge X-ray absorption fine structure spectroscopy and complementary density functional theory calculations the chemical composition and orientational order of adlayers of functionalized azobenzene containing TATA platform molecules were characterized. According to these studies the molecules are chemically intact on the surface after self-assembly from solution and exhibit a well-defined adsorption geometry where the azobenzene units are oriented almost perpendicular to the surface.

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Section: Introductionmentioning

confidence: 99%

X-ray spectroscopy characterization of azobenzene-functionalized triazatriangulenium adlayers on Au(111) surfaces

Ulrich

Jung

Strunskus

et al. 2015

Phys. Chem. Chem. Phys.

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“…Due to their unique (E) / (Z) / (E) isomerization process, the azobenzene derivatives found a wide applicability in many fields such as photoresponsive materials, optical data storage, surface relief gratings, optoelectronics switches, molecular machines, liquid crystal displays, etc. (Rau 1990a ; Kumar & Neckers 1989 ; Bouas-Laurent & Durr 2001 ; Natansohn & Rochon 2002 ; Angiolini et al 2011 ; Ebead 2011 ; Fayet et al 2010 ; Hamelmann et al 2004 ; Matczyszyn et al 2003 ; Kay et al 2007 ; Merino & Ribagorda 2012 ; Wang & Zhang 2012 ; Delaire & Nakatani 2000 ; Luftor et al 2009 ; Ishow et al 2006 ).…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and modeling studies of azobenzene derivatives containing maleimide groups

Cojocaru¹,

Airinei²,

Fifere³

2013

SpringerPlus

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The molecular orbital calculations have been carried out to investigate the structure and stability of (E) / (Z) isomers of some azobenzene derivatives containing maleimide groups. A special attention has been devoted to the compound (E)-1, (E)-1-(4-(phenyldiazenyl)phenyl)-1H-pyrrole-2,5-dione, for which the available crystallographic experimental data have been used to validate the modeling structures computed at the theoretical levels AM1, PM3, RHF/6-31+G(d,p) and B3LYP/6-31+G(d,p). To this end, the discrepancy between experimental and calculated structural parameters has been ascertained in terms of root-mean-square deviation (RMSD). The quantum calculations at the level RHF/6-31+G(d,p) yield the most accurate results on (E)-1 structure giving a deviation error from crystallographic data of about 5.00% for bond lengths and 0.97% for interatomic angles. The theoretical electronic absorption spectra of azobenzene derivatives of concern have been computed by means of configuration-interaction method (CI) at the level of semi-empirical Hamiltonians (AM1 and PM3). Likewise, the molecular energy spectra, electrostatic potential and some quantitative structure activity relationship (QSAR) properties of studied molecules have been computed and discussed in the paper.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-586) contains supplementary material, which is available to authorized users.

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“…Since then, this moiety has been extensively studied experimentally and theoretically [28,29]. The molecule is nearly planar in its thermally stable E conformation, while when irradiated with UV light (λ = 365 nm), produces the Z isomer, which has a bent conformation and a much larger dipole moment [30]. It has been reported that E-Z isomerization of azobenzene moieties could be caused by mechanical stress or electrostatic stimulation [31].…”

Section: Introductionmentioning

confidence: 99%

Molecular Design of Microcapsule Shells for Visible Light-Triggered Release

et al. 2019

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The development of photo-responsive capsules to tune and control the sustained-release of encapsulated actives is a fascinating and challenging route to improve the performances and effectiveness of a wide range of delivery applications. In this work, we report the preparation of visible light-responsive capsules obtained via oil-in-water interfacial polycondensation between modified diacyl-chloride azobenzene moiety and diamine flexible spacer in the presence of cross-linkers with different structures and functionalities. The effect on the release profile of the encapsulated perfume oil was investigated using three flexible spacers with different lengths (1,8-diaminooctane; 1,6-diaminohexane and 1,4-diaminobutane) and two types of cross-linkers (1,3,5-benzenetricarbonyl trichloride and melamine). We analyzed how the properties of microcapsules can be tailored changing the design of the shell structure. Fine tuning of the perfume release profiles was obtained. The changes in capsules size and morphology due to visible light irradiation were monitored via light scattering, optical microscopy and atomic force microscopy. Perfume release was 50% faster in the systems prepared with melamine as the cross-linker. Modelling studies were carried out to support the discussion of the experimental results.

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Light-stimulated switching of azobenzene-containing self-assembled monolayers

Cited by 34 publications

References 16 publications

X-ray spectroscopy characterization of azobenzene-functionalized triazatriangulenium adlayers on Au(111) surfaces

X-ray spectroscopy characterization of azobenzene-functionalized triazatriangulenium adlayers on Au(111) surfaces

Molecular structure and modeling studies of azobenzene derivatives containing maleimide groups

Molecular Design of Microcapsule Shells for Visible Light-Triggered Release

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