N-H…O, C-H… O hydrogen-bonded supramolecular frameworks in 4-fluoroanilinium and dicyclohexylaminium picrate salts

Saminathan, Kolandaivelu; Rajamoni, Jagan; Sivakumar, K.

doi:10.1007/s11224-019-01471-1

Cited by 3 publications

(3 citation statements)

References 14 publications

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“…As for the structures reported in this study the important interactions for the crystal packing were seen as being N-H O and C-H O. Recent studies highlight the importance of both N-H O and C-H O H-bonds to stabilize the supramolecular frameworks of picrate salts [25]. A graphic with the percentage of the contribution for both compounds is presented in Figure S5.…”

Section: Characterization Of Compounds 1 Andmentioning

confidence: 58%

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

2023

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Here, we present the preparation and characterization of two novel picrate salts. Compound 1 (DPK-PA) crystallizes in the triclinic system and centrosymmetric space group P , with unit cell parameters a = 9.378(17) Å, b = 9.790(15) Å, c = 10.141(16) Å, α = 99.63(7)°, β = 99.09(8)° and γ = 102.55(8)°, while the compound 2 (BBBPY-PA) crystallizes in the non-centrosymmetric P2 1 2 1 2 1 space group, orthorhombic unit cell parameters a = 6.3902(6) Å, b = 23.416(3) Å and c = 16.7320(18) Å. Both crystal structures present an ion-pair in the asymmetric unit, one picrate anion, and one bipyridine derivative. In the compound 1 structure, the molecule of DPK presents one intramolecular N1-H…N Hbond that contributes to stabilizing the planar conformation of DPK. The absence of intramolecular Hbonding in compound 2 can be explained by the steric hindrance of the tert-butyl group. For 1 and 2, the crystal packing is stabilized N-H…O strong hydrogen bonding interactions, which could be identi ed by the Hirsh eld Surface analysis and ngerprint plots. The compounds were also studied by UV-Vis and infrared analyses, which may support the statement of the formation of new material. Finally, as an attempt to obtain a molecular system to act as a chemical sensor, we studied the uorescence of both compounds, in solution and in solid state, however, no uorescence was observed.

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Section: Characterization Of Compounds 1 Andmentioning

confidence: 58%

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

2023

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“… 31 Moreover, the shortest C–H···O distances in 8OA and 8OA-N are 2.919 and 2.943 Å (green dashed line), respectively, showing formation of intermolecular hydrogen bonding. 32 As shown in Figure S5b , the distances between naphthalene units and the adjacent pyrimidine are 7.102 and 7.815 Å within 8OA-N (blue dashed line), indicating that there is no intramolecular interaction between naphthalene and the adjacent pyrimidine.…”

Section: Resultsmentioning

confidence: 89%

“…As shown in Figure S5a and b, the intermolecular distance in 8OA is 3.640 Å and that in 8OA-N is 3.661 Å (red dashed line), respectively; both distances are less than 3.800 Å, showing the existence of intermolecular π–π interactions . Moreover, the shortest C–H···O distances in 8OA and 8OA-N are 2.919 and 2.943 Å (green dashed line), respectively, showing formation of intermolecular hydrogen bonding . As shown in Figure S5b, the distances between naphthalene units and the adjacent pyrimidine are 7.102 and 7.815 Å within 8OA-N (blue dashed line), indicating that there is no intramolecular interaction between naphthalene and the adjacent pyrimidine.…”

Section: Resultsmentioning

confidence: 90%

Photophysical Properties of Naphthalene-oxacalix[m]arene and Recognition of Fullerene C₆₀

Lan

Wang

et al. 2022

ACS Omega

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Three different pore sizes of oxacalix[ m ]arene[ n ]pyrimidines modified with a naphthalene substituent were synthesized and characterized by HRMS, 1 H NMR, and single-crystal analysis ( 8OA and 8OA-N ). Steady-state spectroscopy indicates these naphthalene-oxacalix[ m ]arenes exhibit good fluorescence properties, which isattributed to the locally excited (LE) state emission, and electrochemical results show that the photoinduced electron transfer (PET) process occurs from the naphthalene substituent to the linked pyrimidine. Nanosecond transient absorption spectra, singlet oxygen quantum yields (Φ Δ 4OA-N = 45.1%, Φ Δ 6OA-N = 56.6%, and Φ Δ 8OA-N = 65.7%) and theoretical calculations demonstrate that the torsion angle between the donor (naphthalene) and the acceptor (pyrimidine) promotes intersystem crossing (ISC), and the lifetime of the triplet state reaches ca. 8 ms. Interestingly, all three host molecules ( 4OA-N , 6OA-N , and 8OA-N ) showed a high affinity for fullerene C 60 , and significant binding constants in the range of 4.10–6.68 × 10 4 M –1 were obtained by fluorescence titration; in contrast, previous reports indicated that the similar oxacalix[ m ]arene[ n ]pyrimidine scaffold could not efficiently complex with C 60 . In the frontier molecular orbital theory calculations of the supramolecular system of 4OA-N@C 60 , the HOMO is distributed on 4OA-N and the LUMO is localized on fullerene. The calculation results further demonstrated that there are strong interactions between the host and the fullerene guest, which is consistent with the result of the experiments. The characteristic photophysical properties of these novel naphthyl-decorated oxacalix[ m ]arene[ n ]pyrimidines broaden their application field, and the stable host–guest system with fullerene can be applied to supramolecular chemistry.

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Picrate salts with bipyridine derivatives: Intra and intermolecular aspects

Moura

Machado

Corrêa

2022

Preprint

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Here, we present the preparation and characterization of two novel picrate salts. Compound 1 (DPK-PA) crystallizes in the triclinic system and centrosymmetric space group P\(\stackrel{-}{1}\), with unit cell parameters a = 9.378(17) Å, b = 9.790(15) Å, c = 10.141(16) Å, α = 99.63(7)°, β = 99.09(8)° and γ = 102.55(8)°, while the compound 2 (BBBPY-PA) crystallizes in the non-centrosymmetric P212121 space group, orthorhombic unit cell parameters a = 6.3902(6) Å, b = 23.416(3) Å and c = 16.7320(18) Å. Both crystal structures present an ion-pair in the asymmetric unit, one picrate anion, and one bipyridine derivative. In the compound 1 structure, the molecule of DPK presents one intramolecular N1-H…N Hbond that contributes to stabilizing the planar conformation of DPK. The absence of intramolecular Hbonding in compound 2 can be explained by the steric hindrance of the tert-butyl group. For 1 and 2, the crystal packing is stabilized N-H…O strong hydrogen bonding interactions, which could be identified by the Hirshfield Surface analysis and fingerprint plots. The compounds were also studied by UV-Vis and infrared analyses, which may support the statement of the formation of new material. Finally, as an attempt to obtain a molecular system to act as a chemical sensor, we studied the fluorescence of both compounds, in solution and in solid state, however, no fluorescence was observed.

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N-H…O, C-H… O hydrogen-bonded supramolecular frameworks in 4-fluoroanilinium and dicyclohexylaminium picrate salts

Cited by 3 publications

References 14 publications

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

Photophysical Properties of Naphthalene-oxacalix[m]arene and Recognition of Fullerene C₆₀

Picrate salts with bipyridine derivatives: Intra and intermolecular aspects

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N-H…O, C-H… O hydrogen-bonded supramolecular frameworks in 4-fluoroanilinium and dicyclohexylaminium picrate salts

Cited by 3 publications

References 14 publications

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

Photophysical Properties of Naphthalene-oxacalix[m]arene and Recognition of Fullerene C60

Picrate salts with bipyridine derivatives: Intra and intermolecular aspects

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Photophysical Properties of Naphthalene-oxacalix[m]arene and Recognition of Fullerene C₆₀