Synthesis, Self-Assembly, and Characterization of Supramolecular Polymers from Electroactive Dendron Rodcoil Molecules

Messmore, Benjamin W.; Hulvat, James F.; Sone, Eli D.; Stupp, Samuel I.

doi:10.1021/ja049325w

Cited by 261 publications

(195 citation statements)

References 38 publications

Supporting

Mentioning

185

Contrasting

Unclassified

Order By: Relevance

“…There have been recent examples from us and others demonstrating interesting function in assemblies that reach into the macromolecular scale. For example, self-assembly causes a dramatic increase in the conductivity of Aida's hexabenzocoronene nanotubes (Hill et al 2004) and Stupp's dendron-rodcoil ribbons (Messmore et al 2004). Meijer has demonstrated both energy transfer (Hoeben et al 2004) and photo-induced electron transfer (Schenning et al 2002) in supramolecular assemblies of oligo(phenylenevinylene)s. These properties suggest great potential in photovoltaic and other devices.…”

Section: Supramolecular Self-assembly At the Macromolecular Scalementioning

confidence: 99%

“…Other rigid aromatic groups were introduced into the rod, including oligothiophenes, oligo(biphenyl ester)s and oligo(phenylenevinylene)s (Messmore et al 2004). In the oligothiophene derivative 3, self-assembly leads to three orders of magnitude increase in the conductivity of iodine-doped films (figure 9).…”

Section: One-dimensional Assembliesmentioning

confidence: 99%

“…The conductivity of the oligothiophene DRC 3 increases from 8.0!10 K8 S cm K1 in THF (left) to 7.9!10 K5 S cm K1 in the assembled state (right). Reproduced with permission from Messmore et al (2004). result of the networks formed by these 1D assemblies. Self-assembly of PA molecules is further controlled by hydrophobicity of the alkyl tail and hydrogen bonding between adjacent peptides.…”

Section: One-dimensional Assembliesmentioning

confidence: 99%

See 2 more Smart Citations

Supramolecular self-assembly codes for functional structures

Palmer

Velichko

Cruz

et al. 2007

Phil. Trans. R. Soc. A.

102

View full text Add to dashboard Cite

Small-molecule self-assembly has proven to be a rich field for the controlled synthesis of supramolecular objects with the size scale of polymers and interesting properties. Using several recent examples from our laboratory, we discuss the development of chemical structure codes for supramolecular self-assembly objects with defined shapes. The resulting materials formed by these objects are promising for electronic functions and biological functions for regenerative medicine.

show abstract

Section: Supramolecular Self-assembly At the Macromolecular Scalementioning

confidence: 99%

Section: One-dimensional Assembliesmentioning

confidence: 99%

Section: One-dimensional Assembliesmentioning

confidence: 99%

See 1 more Smart Citation

Supramolecular self-assembly codes for functional structures

Palmer

Velichko

Cruz

et al. 2007

Phil. Trans. R. Soc. A.

102

View full text Add to dashboard Cite

show abstract

“…The manipulation and alignment of an anisotropic object using dielectrophoretic forces in an electric field has been successfully accomplished with a variety of different structures including metal and semiconducting nanoparticles [11] and nanowires, [16] DNA molecules, [17] carbon nanotubes, [18,19] block copolymers, [20] ZnO-organic complexes, [21] and dendron rod-coil ribbons. [22] This has recently led, for example, to improved emission properties of single conjugated polymer molecules.[23] The possibility of applying this technique to supramolecularly engineered nanostructures is thus of major interest in view of their reversible self-assembling properties under external stimuli such as temperature and chemical environment. [24] We provide here the first direct quantitative determination of the electric-field-assisted alignment of single organic supramolecular fibers self-assembled at a surface.…”

mentioning

confidence: 99%

Electric‐Field‐Assisted Alignment of Supramolecular Fibers

et al. 2006

View full text Add to dashboard Cite

A molecular wire consisting of a metal/molecule/metal junction can be regarded as the basic building block for future nanoelectronics applications. Alongside the great effort expended in the last ten years on the use of single molecules as electroactive components, [1][2][3] there is also a growing interest centered on the use of supramolecular architectures as electroactive species to bridge metallic electrodes.[4] The supramolecular approach can enhance the mechanical and electronic properties of the wire, which should improve the performance of electronic devices.[ [5][6][7][8][9][10] One major challenge in the study of charge transfer across organic molecules is achieving reproducible attachment between metallic electrodes. Although different electrode pairs have been employed, including break junctions, [3] lithographically tailored nanoelectrodes, [11] and a solid substrate and a conductive tip of an atomic force microscope [12][13][14] or a mercury drop, [15] new, scalable routes to the controlled incorporation of nanometer-scale objects in the gap between nanoelectrodes are required. The manipulation and alignment of an anisotropic object using dielectrophoretic forces in an electric field has been successfully accomplished with a variety of different structures including metal and semiconducting nanoparticles [11] and nanowires, [16] DNA molecules, [17] carbon nanotubes, [18,19] block copolymers, [20] ZnO-organic complexes, [21] and dendron rod-coil ribbons. [22] This has recently led, for example, to improved emission properties of single conjugated polymer molecules.[23] The possibility of applying this technique to supramolecularly engineered nanostructures is thus of major interest in view of their reversible self-assembling properties under external stimuli such as temperature and chemical environment. [24] We provide here the first direct quantitative determination of the electric-field-assisted alignment of single organic supramolecular fibers self-assembled at a surface. We have chosen a gel-forming functionalized 1,3,5-triamide cis,cis-cyclohexane derivative (cyclohexane trisamide gelator (CTG), Fig. 1a) that is known to self-assemble into supramolecular fibers in aqueous solution through the formation of hydrogen bonds. [25,26] Due to its wider applicability for electronic applications, we present here attempts to form similar fibers in an organic solvent. Fibers were deposited from solution onto two gold electrodes arranged in a source-drain geometry with micrometer-scale separation. During deposition, a DC voltage was applied between the two electrodes and the system was cooled below its sol-gel transition temperature (T sol-gel ).In the gel, the three intermolecular hydrogen bonds among the amide moieties of CTGs are both parallel to one another and perpendicular to the plane of the cyclohexane ring (see Fig. 1a inset), endowing strong, self-complementary, and uniaxial intermolecular interactions that are necessary to enforce quasi-1D self-assembly.[27] Since each hydrogen bond has a dipolar...

show abstract

“…[1][2][3] It is clear that the performance of device prototypes based on an ensemble of molecules can be improved by achieving full control of the supramolecular self-organization of the active organic components, and by elucidating and optimizing many other physicochemical properties, such as their complex electronic structure, both at the single-molecule and supramolecular level. In this context, scanning probe microscopy (SPM) offers direct, yet quantitative, mapping of a variety of physicochemical properties with submolecular resolution.…”

mentioning

confidence: 99%