Coordination-directed self-assembly of a simple benzothiadiazole-fused tetrathiafulvalene to low-bandgap metallogels

Amacher, Anneliese; Puigmartí‐Luis, Josep; Geng, Yanfang; Lebedev, Victor; Laukhin, V. N.; Krämer, Karl; Hauser, Jürg; Amabilino, David B.; Decurtins, Silvio; Liu, Shixia

doi:10.1039/c5cc06819c

Cited by 33 publications

(12 citation statements)

References 35 publications

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“…The design of coordination polymers with a predictable secondary building unit (SBU) and dimensionality is a quasi-impossible task but the quest remains of great interest for the discovery of new materials with desired properties such as gas adsorption, [1][2][3][4][5][6][7][8][9] sensing, [10][11][12][13][14][15] thermochromism, [16][17][18][19] magnetism, [20][21][22][23][24] conductivity, [25][26][27][28] redox-activity, 29,30 catalysis, 13,[31][32][33] nonlinear optical behavior 34,35 and luminescence. 8,[36][37][38][39][40] Recent reviews on CPs formed by mono-and dithioethers with CuX salts (X = Cl, Br, I) [41][42][43][44][45][46]…”

Section: Introductionmentioning

confidence: 99%

Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers

et al. 2018

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A structurally unique and strongly luminescent non-porous 3D coordination polymer (CP) [Cu 8 I 8 (methyldithiane) 4 ] n , CP3, has been prepared in a quasi-anticipated manner from 2-methyl-1,3-dithiane, L1, and CuI. This CP incorporates the unprecedented Cu 8 I 8 cluster built upon two side-fused open cubanes. The crystal structure of CP3 has been determined at 100, 150, 200, 250, 300, 350 and 400 K to study the temperature dependence of the Cu•••Cu distances. Two other topological 1D and 2D CPs isomers of formula [{Cu 2 I 2 }(L1) 2 ] n featuring dinuclear {Cu 2 ( 2 -I) 2 } rhomboids were also obtained independently by control of the reaction conditions. These two CPs convert into CP3 in hot PrCN thus indicating that this latter material is the thermodynamic product. While CP1 and CP2 are not emissive, CP3 exhibits an intense luminescence due to the incorporation of the octanuclear Cu 8 I 8 clusters as secondary building units (SBUs) within the network. The photophysical properties of CP3 have been investigated and rationalized by means of DFT and TDDFT computing. Furthermore, the thermal stability of these materials has been studied by ATG and DSC analyses. The Raman spectra of CP1-3 have been recorded in the solid state in the 50 -500 cm -1 region.

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Section: Introductionmentioning

confidence: 99%

Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers

et al. 2018

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“…In general, the rational design behind these examples involves the connection of the TTF unit with groups capable of H-bonding, such as urea [57] or amide groups [58][59][60][61][62][63], to form extended structures. The incorporation of other molecular building blocks commonly used to form physical gels [64][65][66][67] or the use of metal-organic interactions [68][69][70] have also been employed to form TTF-based gels. Moreover, the inclusion of hydrophobic aliphatic chains is also employed to facilitate van der Waals interactions and stabilize the supramolecular aggregates [58][59][60][61][62][63][64][65][66][67][68][69][70][71].…”

Section: Introductionmentioning

confidence: 99%

“…The incorporation of other molecular building blocks commonly used to form physical gels [64][65][66][67] or the use of metal-organic interactions [68][69][70] have also been employed to form TTF-based gels. Moreover, the inclusion of hydrophobic aliphatic chains is also employed to facilitate van der Waals interactions and stabilize the supramolecular aggregates [58][59][60][61][62][63][64][65][66][67][68][69][70][71]. If formation of CT complexes takes place, the TTF unit will bear positive charge, which can alter the interaction of neighboring TTF units and influence the intermolecular interactions arising from other groups involved in the self-assembly process.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

et al. 2018

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In this work, we describe the synthesis, characterization, and self-assembly properties of a new tetrathiafulvalene (TTF)-triglycyl low-molecular-weight (LMW) gelator. Supramolecular organogels were obtained in various solvents via a heating-cooling cycle. Critical gelation concentrations (CGC) (range ≈ 5-50 g/L) and thermal gel-to-sol transition temperatures (T gel) (range ≈ 36-51 • C) were determined for each gel. Fourier transform infrared (FT-IR) spectroscopy suggested that the gelator is also aggregated in its solid state via a similar hydrogen-bonding pattern. The fibrillar microstructure and viscoelastic properties of selected gels were demonstrated by means of field-emission electron microscopy (FE-SEM) and rheological measurements. As expected, exposure of a model xerogel to I 2 vapor caused the oxidation of the TTF unit as confirmed by UV-vis-NIR analysis. However, FT-IR spectroscopy showed that the oxidation was accompanied with concurrent alteration of the hydrogen-bonded network.

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“…For other applications,L iu et al reported BTD-TTF as al owmolecular-weight gelator in the presence of certain transitionmetal halide salts ( Figure 5). [51] This self-assembly process is mainly driven by the coordination ability of the BTD moiety to metal ions. Liu et al reported MP-TTF for application in dyesensitised solar cells ( Figure 5).…”

Section: Ttf Derivatives With Electron-withdrawing Groupsmentioning

confidence: 99%

Semiconducting π‐Extended Tetrathiafulvalene Derivatives

Yamada

Yamashita

Hayashi

et al. 2018

Chemistry A European J

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Tetrathiafulvalene (TTF) has been one of the most studied compounds, since the discovery of electrical conductivity as a charge-transfer complex in combination with tetracyano-p-quinodimethane (TCNQ) in 1973. In 2004, TTF was realized in a new light as an innate semiconductor material, as well as conductor and superconductor material. Because of the ready modification of its core skeleton and better solubility than that of acene compounds, many TTF derivatives have been reported to attain better charge-carrier mobility for field-effect transistor devices. Considering the high charge-carrier mobility of acene and TTF derivatives, annulation of the acene and TTF moieties is expected to improve the charge-carrier mobilities. This Minireview focuses on the syntheses, crystal structures, and electronic properties of state-of-the-art π-extended TTF derivatives, based on the history of the development of TTF derivatives. The relationship between the packing structure and charge-carrier mobilities is also discussed.

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Coordination-directed self-assembly of a simple benzothiadiazole-fused tetrathiafulvalene to low-bandgap metallogels

Cited by 33 publications

References 35 publications

Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers

Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

Semiconducting π‐Extended Tetrathiafulvalene Derivatives

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Coordination-directed self-assembly of a simple benzothiadiazole-fused tetrathiafulvalene to low-bandgap metallogels

Cited by 33 publications

References 35 publications

Control of Structures and Emission Properties of (CuI)n 2-Methyldithiane Coordination Polymers

Control of Structures and Emission Properties of (CuI)n 2-Methyldithiane Coordination Polymers

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

Semiconducting π‐Extended Tetrathiafulvalene Derivatives

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Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers

Control of Structures and Emission Properties of (CuI)_n 2-Methyldithiane Coordination Polymers