Inorganic anion induced supramolecular architectures and luminescent properties of flexible bis(pyridyl) based ionic salts

Deng, Zhao‐Peng; Qi, Hui-Ling; Huo, Li‐Hua; Zhao, Hui; Gao, Shan

doi:10.1039/c1ce05628j

Cited by 26 publications

(19 citation statements)

References 64 publications

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“…In addition, Deng and co-workers have shown how the choice of counter-ion can have an impact on the emission 70 quantum yield in the solid-state for a series of flexible organic fluorophores. 16 They correlated these interactions to a large drop in performance of the device compared to the hexafluorophosphate salt. Clearly subtle changes to both cation and anion affect crystal packing and device performance.…”

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confidence: 99%

Triazole-directed hydrogen-bonded structures of cationic iridium(iii) complexes

2014

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Despite the differing size of the Cland PF 6 counter-ions, the structures of the heteroleptic iridium(III) complexes, [Ir(dFphtl) 2 (btl)]Cl, [1]Cl, and [Ir(dFphtl) 2 (btl)]PF 6, [1]PF 6 , (where dFphtl = 1-Benzyl-4-(2,4-difluorophenyl)-1H-1,2,3triazole and btl = 1,1'-Dibenzyl-4,4'-bi-1H-1,2,3-triazolyl) are found to exhibit similar morphologies in which both structures adopt hydrogen-bonded networks driven by the hydrogen-bond donor and acceptor demands of the triazole functional group. The triazole thus can be used as a supramolecular synthon to control the internuclear distance in the solid-state. The 1,2,3-triazole ring is a ubiquitous building block in modern synthetic chemistry, 1 which is readily constructed via the Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction (Scheme 1). 2 The ability of this reaction to support a diversity of substituents has popularized the use of this reaction as one of the common 'click' reactions coined by Sharpless. 3 Recently the structure-directing properties of the 1,2,3-triazole ring have been explored 1 and, for example, anion-templating of the C(5)-H group has been implemented in organic catalysis, 4 whilst intramolecular hydrogen bonding of the triazole unit has been utilised to enhance anion binding 5 and as anion sensors inter alia. 6

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confidence: 99%

Triazole-directed hydrogen-bonded structures of cationic iridium(iii) complexes

2014

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“…As shown in Fig. 8, the N1-containing cations interact with each other through C-HÁ Á Áp interactions [27] (C11-H11AÁ Á Áp, 3.892(1) Å, \C11-H11AÁ Á Áp = 140.4°) between the p electron density of the N1-containing pyridyl rings and adjacent CH groups, thus generating a double zig-zag chain motif. Meanwhile, a pair of symmetryrelated N4-containing cations form a dimer through N-HÁ Á ÁN bonds between the pyridyl N and pyridyl NH groups (Fig.…”

Section: Crystal Structures Of [Hgx 4 ] 2à á2hl4 + [X = Br (11) and Imentioning

confidence: 98%

“…A close inspection reveals that adjacent N1-containing pyridyl rings are arranged in a point-toface mode. Therefore, the C-HÁ Á Áp interactions [27] (C3-H3AÁ Á Áp, 3.845(1) Å, \C-HÁ Á Áp = 150.0°) between the p electron density of the pyridyl ring and an adjacent CH group extend adjacent layers into a supramolecular network.…”

Section: Crystal Structure Of [Hg(l4)cl 2 ] N (10)mentioning

confidence: 98%

Mercury supramolecular architectures constructed from flexible unsymmetrical bis(pyridyl) ligands: Structural motif mediated by mercury-halide clusters, ligand conformations and non-covalent interactions

Zhang

Huo

et al. 2016

Polyhedron

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“…The nPeOH molecules attach to the chain with the assistance of N− H···O hydrogen bonding interactions and link adjacent chains into a 2-D layer structure through the C−H···π interactions (C27−H27B···π, 3.655(9) Å, ∠C−H···π = 123.4°) between the π electron density of naphthyl rings and adjacent methylene CH groups ( Figure 5). 17 Different from the above five salts, the crystallization of H 2 NDS and TPMA from dioxane solution generates salt 6 with both dioxane and water molecules in the unit cell. Two −SO 3 groups, two −NH 3 groups, two water molecules, and two dioxane molecules in this salt interact with each other through the N−H···O and O−H···O hydrogen bonding interactions to form a finite [(SO 3 ) 2 (NH 3 ) 2 (H 2 O) 2 (DO) 2 ] cluster ( Figure 6).…”

Section: ■ Introductionmentioning

confidence: 99%

Solvent Effect on the Supramolecular Patterns and Luminescent Properties of Organic Salts Comprising Naphthalene-1,5-disulfonic Acid and Triphenylmethylamine

Huo

Deng

et al. 2014

Crystal Growth & Design

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The solvent reaction of naphthalene-1,5-disulfonic acid and triphenylmethylamine gives rise to nine organic salts, namely, 2(HTPMA) + · (NDS) 2− ·2(MeOH) (1), 2(HTPMA) + ·(NDS) 2− ·6(EtOH) (2), 2(HTPMA) + · (NDS) 2− ·4(n-PrOH) (3), 2(HTPMA) + ·(NDS) 2− ·4(n-BuOH) (4), 2-(HTPMA) + ·(NDS) 2− ·2(n-PeOH) (5), 2(HTPMA) + ·(NDS) 2− ·3(DO)· 2(H 2 O) (6), 2(HTPMA) + ·(NDS) 2− ·4(DMF) (7), 2(HTPMA) + ·(NDS) 2− · 4(DMSO) (8), and 2(HTPMA) + ·(NDS) 2− ·4(H 2 O) (9) (H 2 NDS = naphthalene-1,5-disulfonic acid, TPMA = triphenylmethylamine, DO = 1,4-dioxane), which have been characterized by elemental analysis, infrared spectroscopy, thermogravimetric analysis, photoluminescence (PL), and powder and single-crystal X-ray diffraction (XRD). Structural analyses indicate that the nature of the solvent molecules can effectively influence the hydrogen bonding modes of the −SO 3 − and −NH 3 + groups, which then result in diverse architectures. The HTPMA + cations and NDS 2− anions in salts 1, 3, and 4 are alternately arranged to form column motifs, which then pack with each other to form lamellar structures with a wide interlayer space. The NDS 2− anions in salts 2 and 5 adopt standing and recumbent positions and act as pillars to extend adjacent double layers formed by HTPMA + cations into pillared layered supramolecular networks. In comparison, pairs of HTPMA + cations in salt 6 act as pillars and extend the layers formed by two kinds of NDS 2− anions to generate pillared layered frameworks. Salts 7 and 8 exhibit a similar packing diagram, in which adjacent monolayers of HTPMA + cations are pillared by the NDS 2− anions in a recumbent position. Salt 9 is a porous hydrogenbonding organic framework assembled from the alternate arrangement of HTPMA + cations and NDS 2− anions, and its products at 50 and 120°C exhibit different structures after being immersed in aqueous solution with the composition of 2(HTPMA) + · (NDS) 2− ·4(H 2 O) (10) and 2(HTPMA) + ·2(TPMA)·(NDS) 2− (11). Luminescent investigation reveals that the emission maximum of salts 1−9 varies from 382 to 393 nm. Moreover, the detailed chemical behaviors for salt 9, such as thermal stability, temperature-dependent infrared spectroscopy, powder XRD, PL, are carefully studied.

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Inorganic anion induced supramolecular architectures and luminescent properties of flexible bis(pyridyl) based ionic salts

Cited by 26 publications

References 64 publications

Triazole-directed hydrogen-bonded structures of cationic iridium(iii) complexes

Triazole-directed hydrogen-bonded structures of cationic iridium(iii) complexes

Mercury supramolecular architectures constructed from flexible unsymmetrical bis(pyridyl) ligands: Structural motif mediated by mercury-halide clusters, ligand conformations and non-covalent interactions

Solvent Effect on the Supramolecular Patterns and Luminescent Properties of Organic Salts Comprising Naphthalene-1,5-disulfonic Acid and Triphenylmethylamine

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