Efficient Intermolecular Charge Transport in Self-Assembled Fibers of Mono- and Bithiophene Bisurea Compounds

Schoonbeek, Franck S.; Esch, Jan H. van; Wegewijs, B.; Rep, D.B.A.; Haas, Matthijs P. de; Klapwijk, T. M.; Kellogg, Richard M.; Feringa, Ben L.

doi:10.1002/(sici)1521-3773(19990517)38:10<1393::aid-anie1393>3.3.co;2-8

Cited by 87 publications

(126 citation statements)

References 4 publications

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“…[3][4][5][6][7][8][9][10][11] Because π-conjugated compounds tend to aggregate by π-π stacking, the introduction of non-covalent interactions at appropriate positions increases their association constants and facilitates the formation of higher-ordered structures. 12,13 For example, supramolecular gels can be formed through intermolecular interactions such as hydrogen bonds, 14,15 and multiple long alkyl chains facilitate columnar stacking along the π-stacking direction of supramolecular assemblies [16][17][18][19] (Figure 1a). A variety of assembled structures can be formed through covalent linkages between π-conjugated units (Figure 1b).…”

Section: Introductionmentioning

confidence: 87%

π-Conjugated polymer-layered structures: synthesis and self-assembly

Tsuji

Morisaki

Chujo

2016

Polym J

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π-Conjugated polymers capped with a boronic acid end-functional group were synthesized by chain-growth Suzuki-Miyaura polycondensation. The obtained polymers were reacted with a π-stacked-polymer scaffold, developed in our previous work. Despite their bulkiness, the conjugated polymers were efficiently introduced into the polymer scaffold. The spectroscopic and optical characterization of the obtained graft polymers in the solid state revealed that the original π-conjugated polymers were stacked in a single polymer chain. Although excluded volume effects prevented significant intermolecular interactions between the polyfluorenes, the introduced polythiophenes formed intermolecular π-stacked structures. Direct observations of the obtained graft polymers showed that the graft polymers self-assembled into the spherical or fiber structures depending on the introduced polymers, whereas no ordered structures were formed by the same polymers before the polymer reaction.

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Section: Introductionmentioning

confidence: 87%

π-Conjugated polymer-layered structures: synthesis and self-assembly

Tsuji

Morisaki

Chujo

2016

Polym J

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“…Fluorocarbon-oligothiophene isomers containing variously positioned perfluorinated-arene and alkyl substituents [3,4,[49][50][51] are of particular interest as the thiophenebased semiconductors have stabilized LUMO energies in comparison to other heteroatom aromatics, as well as other favorable properties including chemical and thermal stability, synthetic tailorability, and relatively large carrier mobilities. [3,4,[51][52][53][54][55][56] Indeed, substantial mobilities and n-type carrier dominance have been observed in these materials, a striking variance from the p-type transport typical of unfunctionalized and hydrocarbon-functionalized oligothiophenes. [48,[52][53][54][55]57,58] In this contribution, we focus on the structural, electronic, and transport properties of three electrically and crystallographically characterized mixed-polarity molecules with perfluoroarene groups sequentially located at different skeletal positions; each molecule contains six rings, two perfluoroarene units and four thiophene rings (see Fig.…”

Section: Full Papermentioning

confidence: 99%

Modeling Electron and Hole Transport in Fluoroarene‐Oligothiopene Semiconductors: Investigation of Geometric and Electronic Structure Properties

Koh

Risko

Filho

et al. 2008

Adv Funct Materials

110

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A theoretical study using density functional theory is undertaken to gain insight into how the structural, electronic, and electron‐transfer characteristics of three Fluoroarene‐oligothiophene semiconductors influence the preferred transport of electrons versus holes in field‐effect transistor applications. The intermolecular electronic coupling interactions are analyzed through both a simplified energy‐splitting in dimer (ESID) model and as a function of the entire dimer Hamiltonian in order to understand the impact of site energy differences; our results indicate that these differences are generally negligible for the series and, hence, use of the ESID model is valid. In addition, we also investigate the reduction and oxidation processes to understand the magnitudes of the intramolecular reorganization energy for the charge‐hopping process and expected barrier heights for electron and hole injection into these materials. From the electronic coupling and intramolecular reorganization energies, estimates of the nearest‐neighbor electron‐transfer hopping rate constant for electrons are obtained. The ionization energetics suggest favored electron injection for the system with perfluoroarene groups at the end of the thiophene core, in agreement with experiments. The combined analyses of the electron‐transfer properties and ionization processes suggest possible ambipolar behavior for these materials under favorable device conditions.

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“…[16] Organogels based on LMWGs with functional groups have been the target of increasing attention in recent years because of various potential applications as soft materials. [17][18][19][20][21][22][23][24][25][26][27][28][29][30] For instance, photochromic organogels featuring bisthienylethene with intriguing optical properties have been studied. [31][32][33] Some SP-functionalized macromolecular gels have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Light‐Triggered Self‐Assembly of a Spiropyran‐Functionalized Dendron into Nano‐/Micrometer‐Sized Particles and Photoresponsive Organogel with Switchable Fluorescence

Chen

Zhang

et al. 2009

Adv Funct Materials

123

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The synthesis, self‐assembly, and spectroscopic investigations of spiropyran (SP)‐functionalized dendron 1 are reported. Under UV light irradiation, assembly of 1 into nano‐/microparticles occurs due to the transformation of the closed form of SP into the open merocyanine (MC) form. The formation of these nano‐/microparticles is confirmed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) experiments in addition to the confocal laser scanning microscopy (CLSM) measurements. These nano‐/microparticles exhibit relatively strong red emission. It is interesting to note that the direct cooling of the toluene/benzene solution of 1 to 0 °C leads to gel formation. Multivalent π–π interactions due to the dendron in 1 may be the driving‐force for the gelation. The UV light irradiation cannot destroy the gel phase, and in fact, the gel–gel transition is successfully realized. The purple‐blue gel exhibits relatively strong red fluorescence; moreover, the fluorescence can be reversibly switched by alternating UV and visible light irradiation. The results clearly indicate that the MC form after aggregation becomes more stable and fluorescent.

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Efficient Intermolecular Charge Transport in Self-Assembled Fibers of Mono- and Bithiophene Bisurea Compounds

Cited by 87 publications

References 4 publications

π-Conjugated polymer-layered structures: synthesis and self-assembly

π-Conjugated polymer-layered structures: synthesis and self-assembly

Modeling Electron and Hole Transport in Fluoroarene‐Oligothiopene Semiconductors: Investigation of Geometric and Electronic Structure Properties

Light‐Triggered Self‐Assembly of a Spiropyran‐Functionalized Dendron into Nano‐/Micrometer‐Sized Particles and Photoresponsive Organogel with Switchable Fluorescence

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