Towards supramolecular electronics

Schenning, Albertus P. H. J.; Jonkheijm, Pascal; Hoeben, Freek J. M.; Herrikhuyzen, Jeroen van; Meskers, Stefan C. J.; Meijer, E. W.; Herz, Laura M.; Clément, Daniel; Silva, C.; Phillips, R. T.; Friend, Richard H.; Beljonne, David; Miura, Atsushi; Feyter, Steven De; Zdanowska, Magdalena; Uji‐i, Hiroshi; Schryver, F. C. De; Chen, Z.; Würthner, Frank; Mas‐Torrent, Marta; Boer, Duncan den; Durkut, M.; Hadley, P.

doi:10.1016/j.synthmet.2004.06.038

Cited by 51 publications

(40 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The chirality of the solvent directs the macroscopic chirality of the monolayer (15). After these results, we focus on the current challenge in surface chirality, which includes understanding the underlying driving force for the chiral formation, amplification, transition, and controlling the chiral structure.Recently, oligo(p-phenylenevinylene) (OPV) and its derivatives have attracted a lot of attention because of their advanced optical and electronic properties and possible application in organic electronic devices (16)(17)(18). In the present report, an aldehyde-substituted OPV molecule (OPV3-CHO, Scheme 1) is used as a model compound to study its structure on a solid surface.…”

mentioning

confidence: 99%

“…Recently, oligo(p-phenylenevinylene) (OPV) and its derivatives have attracted a lot of attention because of their advanced optical and electronic properties and possible application in organic electronic devices (16)(17)(18). In the present report, an aldehyde-substituted OPV molecule (OPV3-CHO, Scheme 1) is used as a model compound to study its structure on a solid surface.…”

mentioning

confidence: 99%

“…To achieve a unified assembly with a single structure, an efficient method is proposed by coadsorption of OPV3-CHO with selected molecules. For example, an assembly with side-by-side helix structure is formed by a simple coadsorption of OPV3-CHO with alkyl bromide (C n H 2nþ1 Br, n ¼ [15][16][17][18]. The experiments by cocrystallization of OPV3-CHO∕ C n H 2nþ1 X (X ¼ Cl, Br, and I) show the important role of halogen bonding in formation of the uniform structure.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy

Chen

Wang

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

OPV3-CHO molecules are employed to prepare assembly on highly oriented pyrolytic graphite, and the so-prepared assembly is investigated by scanning tunneling microscopy. In the assembly chiral domains are observed with various structures such as linear and windmill. The chiral structural formation, stability, transition, and possible unification are intensively studied. After thermal annealing, linear structure was the only structure. To achieve a unified assembly with a single structure, an efficient method is proposed by coadsorption of OPV3-CHO with selected molecules. For example, an assembly with side-by-side helix structure is formed by a simple coadsorption of OPV3-CHO with alkyl bromide (C n H 2nþ1 Br, n ¼ 15-18). The experiments by cocrystallization of OPV3-CHO∕ C n H 2nþ1 X (X ¼ Cl, Br, and I) show the important role of halogen bonding in formation of the uniform structure. The results are significant in understanding the intermolecular noncovalent interactions that dominate the surface structure and chirality.coadsorption | halogen bonding | surface chirality U nderstanding the formation and structural transition of molecular nanostructure is an important issue in chemistry, molecular science, and nanodevice fabrication. Among various molecular nanostructures, two-dimensional surface chirality is a property of asymmetry and of great interest in fundamental research and industrial application such as life genesis, nonlinear optics, enantioselective heterogeneous catalysis, and surface modification (1-3). With atomic resolution, scanning tunneling microscopy (STM) is powerful in surface chirality study (4-7). From absolute chirality determination to chiral structure fabrication with chiral molecules or achiral molecules on a solid surface, a few results have been reported (8-13). Xu et al. directly observed the chirality of (R)-and (S)-2-phenylpropionamide molecules on Cu(111) in solution by using electrochemical STM (14). De Feyter et al. studied solvent-induced homochirality in selfassembled monolayers of achiral molecules. The chirality of the solvent directs the macroscopic chirality of the monolayer (15). After these results, we focus on the current challenge in surface chirality, which includes understanding the underlying driving force for the chiral formation, amplification, transition, and controlling the chiral structure.Recently, oligo(p-phenylenevinylene) (OPV) and its derivatives have attracted a lot of attention because of their advanced optical and electronic properties and possible application in organic electronic devices (16)(17)(18). In the present report, an aldehyde-substituted OPV molecule (OPV3-CHO, Scheme 1) is used as a model compound to study its structure on a solid surface. It is found that achiral OPV3-CHO can form chiral domains on highly oriented pyrolytic graphite (HOPG). The OPV3-CHO adlayer is investigated by STM including structural formation, stability, transition, and possible unification of the chiral domains. The OPV3-CHO chiral domains appear in linear and windmil...

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy

Chen

Wang

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

show abstract

“…We used the same experimental conditions as previous studies ͑temperature around 14°C and concentrations between 10 −5 M and 10 −4 M͒ which investigated these supramolecular stacks. 7,[15][16][17][18] Small-angle neutron scattering experiments showed cylindrical architectures with average stack lengths of 150 nm and radius 3 nm for MOPV4, and 60 nm and radius 2.5 nm for MOPV3. For MOPV derivatives, the cylinders consist of stacked dimers in a helical fashion based on the observed circular dichroism.…”

Section: Resultsmentioning

confidence: 99%

“…7,[15][16][17][18] We have demonstrated that resonance energy transfer between MOPV derivatives of different length ͑and exciton energies͒ is greatly enhanced by supramolecular assembly. At low MOPV4 mole fraction ͑Շ2.5% ͒, isolated MOPV4 chromophores are incorporated into MOPV3 helical assemblies as long as the solution is thermally cycled to dissolve and then re-assemble the stacks.…”

mentioning

confidence: 99%

The effects of supramolecular assembly on exciton decay rates in organic semiconductors

Clément

Makereel

Herz

et al. 2005

The Journal of Chemical Physics

View full text Add to dashboard Cite

We present time-resolved photoluminescence measurements on two series of oligop-phenylenevinylene ͑OPV͒ materials that are functionalized with quadruple hydrogen-bonding groups. These form supramolecular assemblies with thermotropic reversibility. The morphology of the assemblies depends on the way that the oligomers are functionalized; monofunctionalized OPVs ͑MOPVs͒ form chiral, helical stacks while bifunctionalized OPVs ͑BOPVs͒ form less organized structures. These are therefore model systems to investigate the effects of supramolecular assembly, the effects of morphology, and the dependence of oligomer length on the radiative and nonradiative rates of -conjugated materials. The purpose of this work is to use MOPV and BOPV derivatives as model systems to study the effect of intermolecular interactions on the molecular photophysics by comparing optical properties in the dissolved phase and the supramolecular assemblies. A simple photophysical analysis allows us to extract the intrinsic radiative and nonradiative decay rates and to unravel the consequences of interchromophore coupling with unprecedented detail. We find that interchromophore coupling strongly reduces both radiative and intrinsic nonradiative rates and that the effect is more pronounced in short oligomers.

show abstract