TY  - JOUR
A1  - Herder, Martin
A1  - Utecht, Manuel Martin
A1  - Manicke, Nicole
A1  - Grubert, Lutz
A1  - Pätzel, Michael
A1  - Saalfrank, Peter
A1  - Hecht, Stefan
T1  - Switching with orthogonal stimuli electrochemical ring-closure and photochemical ring-opening of bis(thiazolyl) maleimides
JF  - Chemical science
N2  - The photochemistry as well as electrochemistry of novel donor-acceptor bis(morpholinothiazolyl)maleimides has been investigated. Proper substitution of these diarylethene-type molecular switches leads to the unique situation in which their ring-closure can only be accomplished electrochemically, while ring-opening can only be achieved photochemically. Hence, these switches operate with orthogonal stimuli, i.e. redox potential and light, respectively. The switch system could be optimized by introducing trifluoromethyl groups at the reactive carbon atoms in order to avoid by-product formation during oxidative ring closure. Both photochemical and electrochemical pathways were investigated for methylated, trifluoromethylated, and nonsymmetrical bis(morpholinothiazolyl) maleimides as well as the bis(morpholinothiazolyl) cyclopentene reference compound. With the aid of the nonsymmetrical "mixed" derivative, the mechanism of electrochemically driven ring closure could be elucidated and seems to proceed via a dicationic intermediate generated by two-fold oxidation. All experimental work has been complemented by density functional theory that provides detailed insights into the thermodynamics of the ring-open and closed forms, the nature of their excited states, and the reactivity of their neutral as well as ionized species in different electronic configurations. The particular diarylethene systems described herein could serve in multifunctional (logic) devices operated by different stimuli (inputs) and may pave the way to converting light into electrical energy via photoinduced "pumping" of redox-active meta-stable states.
Y1  - 2013
U6  - https://doi.org/10.1039/c2sc21681g
SN  - 2041-6520
VL  - 4
IS  - 3
SP  - 1028
EP  - 1040
PB  - Royal Society of Chemistry
CY  - Cambridge
ER  - 
TY  - JOUR
A1  - Lange, Ilja
A1  - Reiter, Sina
A1  - Paetzel, Michael
A1  - Zykov, Anton
A1  - Nefedov, Alexei
A1  - Hildebrandt, Jana
A1  - Hecht, Stefan
A1  - Kowarik, Stefan
A1  - Woell, Christof
A1  - Heimel, Georg
A1  - Neher, Dieter
T1  - Tuning the work function of polar zinc oxide surfaces using modified phosphonic acid self-assembled monolayers
JF  - Advanced functional materials
N2  - Zinc oxide (ZnO) is regarded as a promising alternative material for transparent conductive electrodes in optoelectronic devices. However, ZnO suffers from poor chemical stability. ZnO also has a moderate work function (WF), which results in substantial charge injection barriers into common (organic) semiconductors that constitute the active layer in a device. Controlling and tuning the ZnO WF is therefore necessary but challenging. Here, a variety of phosphonic acid based self-assembled monolayers (SAMs) deposited on ZnO surfaces are investigated. It is demonstrated that they allow the tuning the WF over a wide range of more than 1.5 eV, thus enabling the use of ZnO as both the hole-injecting and electron-injecting contact. The modified ZnO surfaces are characterized using a number of complementary techniques, demonstrating that the preparation protocol yields dense, well-defined molecular monolayers.
KW  - ZnO
KW  - self-assembled monolayers
KW  - phosphonic acid
KW  - surface modification
KW  - electrodes
Y1  - 2014
U6  - https://doi.org/10.1002/adfm.201401493
SN  - 1616-301X
SN  - 1616-3028
VL  - 24
IS  - 44
SP  - 7014
EP  - 7024
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Lange, Ilja
A1  - Reiter, Sina
A1  - Kniepert, Juliane
A1  - Piersimoni, Fortunato
A1  - Paetzel, Michael
A1  - Hildebrandt, Jana
A1  - Brenner, Thomas J. K.
A1  - Hecht, Stefan
A1  - Neher, Dieter
T1  - Zinc oxide modified with benzylphosphonic acids as transparent electrodes in regular and inverted organic solar cell structures
JF  - Applied physics letters
N2  - An approach is presented to modify the work function of solution-processed sol-gel derived zinc oxide (ZnO) over an exceptionally wide range of more than 2.3 eV. This approach relies on the formation of dense and homogeneous self-assembled monolayers based on phosphonic acids with different dipole moments. This allows us to apply ZnO as charge selective bottom electrodes in either regular or inverted solar cell structures, using poly(3-hexylthiophene): phenyl-C71-butyric acid methyl ester as the active layer. These devices compete with or even surpass the performance of the reference on indium tin oxide/poly(3,4-ethylenedioxythiophene) polystyrene sulfonate. Our findings highlight the potential of properly modified ZnO as electron or hole extracting electrodes in hybrid optoelectronic devices. (C) 2015 AIP Publishing LLC.
Y1  - 2015
U6  - https://doi.org/10.1063/1.4916182
SN  - 0003-6951
SN  - 1077-3118
VL  - 106
IS  - 11
PB  - American Institute of Physics
CY  - Melville
ER  -