A Low-Molecular-Mass Gelator with an Electroactive Tetrathiafulvalene Group:  Tuning the Gel Formation by Charge-Transfer Interaction and Oxidation

Wang, Cheng; Zhang, Deqing; Zhu, Daoben

doi:10.1021/ja055800u

Cited by 253 publications

(133 citation statements)

References 20 publications

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“…Since Feringa and co-workers pioneeringly succeeded in fabricating the conductive nanofibers from (oligo)thiophene-functionalized bisureas, [22] several functional molecules including OPVs have been combined with these structure-directing agents to obtain extended one-dimensional nanostructures. [23,24] On the other hand, TDP wedges act as van der Waals interaction sites with strong solubilizing and phase-separating properties (Scheme 1a). [16,25] Thus, symmetrical substitution of the bisurea unit by OPV and TDP moieties as in 1 a would allow highly efficient supramolecular polymerization driven by cooperative noncovalent interactions on both sides in the molecule (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Yagai

Kubota

Iwashima

et al. 2008

Chemistry A European J

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Bis- and monoureas hybridized with the oligo(p-phenylene vinylene) (OPV) pi-electronic segment and 3,4,5-tridodecyloxyphenyl wedge were synthesized and their supramolecular polymerization in diluted solution, gel formation in concentrated solution, and liquid crystallinity in bulk state were investigated. Bisurea 1a featuring a hexamethylene linker showed the highest supramolecular polymerization ability and formed tapelike nanofibers that can gelate various organic solvents. On the other hand, bisurea 1b featuring a dodecamethylene linker and monourea 2 showed a lower degree of supramolecular polymerization, resulting in gel formations in a smaller variety of solvents. These results clearly reflect a high level of cooperativity between the two urea sites and the two OPV segments of 1a upon hydrogen-bonding and pi-pi stacking interactions, respectively. When the gels of 1a, 1b, and 2 were dried, all the compounds self-organized into multilamellar superstructures. Thermal treatment of these lamellae at high temperatures induces columnar liquid-crystalline mesophases as a result of microsegregation between the rigid OPV parts and the molten aliphatic wedges. These results demonstrate that the present molecular constituent is very useful for fabricating dye-based functional assemblies providing nanoscale pi-electronic fibers, and solvent-incorporated and bulk soft materials.

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Section: Introductionmentioning

confidence: 99%

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Yagai

Kubota

Iwashima

et al. 2008

Chemistry A European J

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“…[15][16][17][18][19] For example, Jør-gensen et al 15 reported the gel formation of bis-arborols substituted TTF in ethanol/water or DMF/water in 1994. We early reported a TTF derivative with a urea moiety, which can gel several organic solvents; in particular, the corresponding solution-gel phase transition can be tuned by oxidation and reduction as well by reactions with electron acceptors.…”

Section: -14mentioning

confidence: 99%

Cholesterol‐substituted Tetrathiafulvalene (TTF) Compound: Formation of Organogel and Supramolecular Chirality

Wang¹,

Sun²,

Zhang³

et al. 2010

Chin. J. Chem.

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A new tetrathiafulvalene (TTF) derivative with two cholesterol units (compound 1) was synthesized and characterized. Gelation of n-hexane occurred after the hot solution of 1 was subjected to ultrasonic treatment for a few minutes. The resulting organogel was characterized with SEM, XRD and AFM. Besides heating the gel-sol transition also occurred upon addition of I 2 which can oxidize the TTF unit in 1. This result provides a new example of organogels responding to redox reactions. Interestingly, gelation-induced CD signals were observed and the CD signals can be tuned with the gel-sol transition which can be effected by heating and chemical reaction with I 2 .

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“…Tetrathiafulvalene (TTF) derivatives are in turn, remarkable semiconductors for preparing devices as Field Effect Transistors [18][19][20][21][22] and the obtained results already point out the high potential of these materials, which can be easily procesed [23] and tailored synthesized. [24] Even though nanostructuration of TTF derivatives in different surfaces has been demonstrated, [25][26][27][28] potential applications of TTFs as component in circuitry do still require methods for precise nanoscale controlled position and/or manipulation of those molecules.…”

Section: Introductionmentioning

confidence: 99%

Sub-50 nm positioning of organic compounds onto silicon oxide patterns fabricated by local oxidation nanolithography

Losilla¹,

Oxtoby²,

Martínez³

et al. 2008

Nanotechnology

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We present a process to fabricate molecule-based nanostructures by merging a bottom-up interaction and a top-down nanolithography. Direct nanoscale positioning arises from the attractive electrostatic interactions between the molecules and silicon dioxide nanopatterns. Local oxidation nanolithography is used to fabricate silicon oxide domains with variable gap separations ranging from 40 nm to several microns in length. We demonstrate that a ionic tetrathiafulvalene (TTF) semiconductor can be directed from a macroscopic liquid solution (1 M) and selectively deposited onto predefined nanoscale regions of a 1 cm 2 silicon chip with an accuracy of 40 nm.

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A Low-Molecular-Mass Gelator with an Electroactive Tetrathiafulvalene Group: Tuning the Gel Formation by Charge-Transfer Interaction and Oxidation

Abstract: A new low-molecular-mass gelator with one TTF and one urea group is described. It was found that the gel formation can be tuned by formation of CT complexes and oxidation.

Cited by 253 publications

References 20 publications

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Supramolecular Polymerization and Polymorphs of Oligo(p‐phenylene vinylene)‐Functionalized Bis‐ and Monoureas

Cholesterol‐substituted Tetrathiafulvalene (TTF) Compound: Formation of Organogel and Supramolecular Chirality

Sub-50 nm positioning of organic compounds onto silicon oxide patterns fabricated by local oxidation nanolithography

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