Self-assembly Molecular Complex by 3,6-Di(pyridin-4-yl)-1,2,4,5-tetrazine with Trimesic Acid through H-Bonding

Hsu, Chia‐Jung; Tang, Shang-Wei; Wang, Jau-Shuenn; Wang, Wen-Jwu

doi:10.1080/15421400600788724

Cited by 14 publications

(3 citation statements)

References 13 publications

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“…Experimental details: With the exception of 1,4-bis(4-pyridyl)benzene, the organic bridges (NLN) were used as received from commercial suppliers or made in house by literature methods. [22][23][24] For 1,4-bis(4-pyridyl)benzene (used in 9), 1,4-dibromobenzene (0.148 g, 0.63 mmol), pyridyl 4-boronic acid (0.20 g, 1.89 mmol), PdA C H T U N G T R E N N U N G (PPh 3 ) 4 (0.032 g, 0.046 mmol), Na 2 CO 3(aq) (1.52 mL, 1 m, 3.04 mmol) and a solvent mixture of DME/H 2 O/EtOH = 7:3:2 (14.4 mL) were sealed in a 20 mL microwave vial and heated for 30 min at 160 8C. The mixture was then filtered to remove the catalyst and washed with ethyl acetate.…”

Section: Methodsmentioning

confidence: 99%

Chemical Control of Spin Propagation between Heterometallic Rings

Faust

Bellini

Candini

et al. 2011

Chemistry A European J

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We present a synthetic, structural, theoretical, and spectroscopic study of a family of heterometallic ring dimers which have the formula [{Cr(7)NiF(3)(Etglu)(O(2)CtBu)(15)}(2)(NLN)], in which Etglu is the pentadeprotonated form of the sugar N-ethyl-D-glucamine, and NLN is an aromatic bridging diimine ligand. By varying NLN we are able to adjust the strength of the interaction between rings with the aim of understanding how to tune our system to achieve weak magnetic communication between the spins, a prerequisite for quantum entanglement. Micro-SQUID and EPR data reveal that the magnetic coupling between rings is partly related to the through-bond distance between the spin centers, but also depends on spin-polarization mechanisms and torsion angles between aromatic rings. Density functional theory (DFT) calculations allow us to make predictions of how such chemically variable parameters could be used to tune very precisely the interaction in such systems. For possible applications in quantum information processing and molecular spintronics, such precise control is essential.

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Section: Methodsmentioning

confidence: 99%

Chemical Control of Spin Propagation between Heterometallic Rings

Faust

Bellini

Candini

et al. 2011

Chemistry A European J

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“…Interestingly, similar strong contacts are present in a crystal structure containing L and trimesic acid, for which the formation of salt bridges is not indicated [ 29 ], as well as in the crystal structures of the analogous 2,2′-(1,2,4,5-tetrazine-3,6-diyl)dipyridine protonated ligand in the presence of nitrate [ 30 ], perchlorate [ 31 ] and tetrabromoterephthalic acid [ 32 ].…”

Section: Resultsmentioning

confidence: 94%

Network Formation via Anion Coordination: Crystal Structures Based on the Interplay of Non-Covalent Interactions

Savastano

Bazzicalupi²,

Mariani³

et al. 2018

Molecules

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We describe the synthesis and the structural characterization of new H2L(CF3CO2)2 (1) and H2L(Ph2PO4)2 (2) compounds containing the diprotonated form (H2L2+) of the tetrazine-based molecule 3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine. X-ray diffraction (XRD) analysis of single crystals of these compounds showed that H2L2+ displays similar binding properties toward both anions when salt bridge interactions are taken into account. Nevertheless, the different shapes, sizes and functionalities of trifluoroacetate and diphenyl phosphate anions define quite different organization patterns leading to the peculiar crystal lattices of 1 and 2. These three-dimensional (3D) architectures are self-assembled by a variety of non-covalent forces, among which prominent roles are played by fluorine–π (in 1) and anion–π (in 2) interactions.

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“…1 HNMR spectra were recorded on aB ruker AC-500 MHz NMR spectrometer.S olution pH was determined by means of abenchtop pH/mV meter 210 from Bante Co. Synthesis 3,6-Di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine (H 2 DPT), used as a spacer,w as synthesized according to techniques reported previously. [23] Synthesis of [Zn(OBA)(H 2 DPT) 0.5 ]·DMF (TMU-34) TMU-34 powder was synthesized from am ixture of Zn(CH 3 COO) 2 ·2H 2 O( 0.22 g, 1mmol), H 2 OBA (0.26 g, 1mmol), and H 2 DPT (0.24 g, 1mmol) in DMF (30 mL). The mixture was sonicated for 160 min at ambient temperature and atmospheric pressure.…”

Section: Materials and Characterizationmentioning

confidence: 99%

Stimuli‐Responsive Metal–Organic Framework (MOF) with Chemo‐Switchable Properties for Colorimetric Detection of CHCl₃

Razavi

Masoomi

Morsali

2017

Chemistry A European J

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The ligands 3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine (H DPT), as a pillar spacer, and 4,4'-oxybis(benzoic acid) (H OBA), as a dicarboxylate linker, have been used to develop a dihydrotetrazine-functionalized pillared metal-organic framework (MOF), [Zn(OBA)(H DPT) ]⋅DMF (TMU-34), as a functionally convertible stimuli-responsive MOF-based sensor. Sonochemically synthesized TMU-34 powder has been employed in the sensing of volatile organic compounds (VOCs). The results show that TMU-34 can act as a solid-state, naked-eye visual chemosensor for the detection of chloroform in the liquid and gas phases. TMU-34, as a chemo-switchable MOF with rapid response, undergoes a significant color change from yellow to pink through reversible dynamic conversion of dihydrotetrazine into tetrazine upon exposure to chloroform in the presence of other VOCs. Whereas other colorimetric MOF-based sensors show a wide range of color changes in the presence of different analytes, TMU-34 undergoes a color change only in the presence of chloroform. A mechanism for the observed color change is proposed on the basis of UV/Vis and H NMR spectroscopic studies. These observations reveal that TMU-34 represents one of the most promising candidates for the highly selective and sensitive detection of chloroform.

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Self-assembly Molecular Complex by 3,6-Di(pyridin-4-yl)-1,2,4,5-tetrazine with Trimesic Acid through H-Bonding

Cited by 14 publications

References 13 publications

Chemical Control of Spin Propagation between Heterometallic Rings

Chemical Control of Spin Propagation between Heterometallic Rings

Network Formation via Anion Coordination: Crystal Structures Based on the Interplay of Non-Covalent Interactions

Stimuli‐Responsive Metal–Organic Framework (MOF) with Chemo‐Switchable Properties for Colorimetric Detection of CHCl₃

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Self-assembly Molecular Complex by 3,6-Di(pyridin-4-yl)-1,2,4,5-tetrazine with Trimesic Acid through H-Bonding

Cited by 14 publications

References 13 publications

Chemical Control of Spin Propagation between Heterometallic Rings

Chemical Control of Spin Propagation between Heterometallic Rings

Network Formation via Anion Coordination: Crystal Structures Based on the Interplay of Non-Covalent Interactions

Stimuli‐Responsive Metal–Organic Framework (MOF) with Chemo‐Switchable Properties for Colorimetric Detection of CHCl3

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Product

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Stimuli‐Responsive Metal–Organic Framework (MOF) with Chemo‐Switchable Properties for Colorimetric Detection of CHCl₃