Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro[benzo[f]chromene-3,2′-indoline

Asiri, Abdullah M.; Ersanlı, Cem Cüneyt; Şahın, Onur; Arshad, Muhammad Nadeem; Hameed, Salem A.

doi:10.1016/j.molstruc.2016.01.086

Cited by 18 publications

(6 citation statements)

References 32 publications

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“…The chromene plane can bend either towards the geminal methyl groups or away from these. Focusing on chromene heterocyles of structural related entries in the CSD (CUTQUQ01 [4], CUTCUQ 02 [10], FURBUP [11], KACLOQ [12], KOCWOO [13]) the same flexibility of the angle is observed (Figure 6b). However, in all structures the typical weakening of the CSpiro-O bond to 1.47 Å is observed, which correspond to the bond length indicated for spiropyrans and spirooxazines in all known crystal structures of the CSD.…”

Section: Discussionmentioning

confidence: 81%

“…Figures of the asymmetric unit and crystal packing was created by using XP in SHELXTL-Plus [19] and Mercury [20]. In (III), both -CH2-CH2-OH side chains in position N20A/B are disordered over several positions [site-occupancy factor for the major-occupied orientation = 0.654 (14) for A and 0.667 (10) for B]. A large cavity is present in the crystal structure (508 Å 3 ).…”

Section: Analysis Of Structural Parametersmentioning

confidence: 99%

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A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

et al. 2017

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Abstract:In this work, crystal structures of commercially available photochromic compounds, i.e., spiropyrans and spirooxazines, were investigated by single-crystal X-ray diffraction. A total of five new structures were obtained via isothermal evaporation experiments under different conditions, namely 1,3,3-Trimethylindolino-benzopyrylospiran (I), 1,3,3-Trimethylindolinonaphtospirooxaxine (II), 1-(2-Hydroxyethyl)-3,3-dimethylindolino-6 -nitrobenzopyrylospiran (III), and 1,3,3-Trimethylindolino-8 -methoxybenzopyrylospiran (IVa and IVb). Since the basic structure of a spiropyran/-oxazine does not present typical hydrogen bond accepting and donating groups, this study illustrates the importance of additional functional groups connected to this kind of molecules to induce specific intermolecular interactions. Our results show that possible hydrogen bonding interactions are rather weak due to the high steric demand of these compounds. These results are supported by a search of the Cambridge structural database focused on related structures.

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Section: Discussionmentioning

confidence: 81%

Section: Analysis Of Structural Parametersmentioning

confidence: 99%

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

et al. 2017

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“…The HOMO and LUMO energies play a vital role in determining the chemical stability of the molecule. HOMO represents the ability to donate an electron and LUMO represents the ability to accept an electron (Asiri et al, 2016). The energy difference between HOMO and LUMO is called the band gap energy (ÁE = E LUMO À E HOMO ).…”

Section: Quantum Chemistry Calculations -Frontier Molecular Orbital (mentioning

confidence: 99%

Seven new metal–organic frameworks assembled from semi-rigid polycarboxylate and auxiliary N-donor ligands: syntheses, structures and properties

Zhang

Yang

Meng

et al. 2020

Acta Crystallogr Sect B

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Seven new metal–organic frameworks (MOFs), namely, [Zn2(L 1)(H2O)3] n (1), [Zn2(L 1)(dib)(H2O)2] n (2), {[Zn2(L 1)(4,4′-bipy)(H2O)2]·H2O} n (3), [Cd2(L 1)(1,10-phen)] n (4), [Ni2(HL 1)(4,4′-bipy)(μ3-OH)(μ2-H2O)] n (5), {[Co4(L 1)(4,4′-bibp)3]·(4,4′-bibp)3} n (6), and [Co2(L 2)(4,4′-bibp)2(H2O)] n (7), where H4 L 1 and H4 L 2 are semi-rigid 3-(3,5-dicarboxylphenoxy)phthalic acid and 4-(3,5-dicarboxylphenoxy)phthalic acid, respectively, and 4,4′-bipy is 4,4′-bipyridine, dib is 1,4-bis(1H-imidazol-1-yl)benzene, 1,10-phen is 1,10-phenanthroline and 4,4′-bipb is 1,4-bis(pyridin-4-yl)benzene, have been prepared under solvothermal conditions with ZnII, CdII, CoII and NiII ions in the presence of auxiliary N-donor ligands. The crystal structures and photoluminescence and magnetic properties of these compounds have been investigated. Compound 1 displays a 3,4,6-connected two-dimensional (2D) topology with a Schläfli symbol of (42.5)2(43.52.7)(45.56.63)2, and the 2D structure was further assembled to form a three-dimensional (3D) framework by intermolecular O—H...O hydrogen bonds. Compound 2 features a novel 3,3,4-connected structure and the point symbol is (4.102)(4.6.84)(62.8). Compound 3 exhibits a 3,4,6-connected 3-nodal net having a 3,4,6 T53 type topology, with the point symbol (4.62)2(42.64)2(42.68.82.103). Compound 4 shows a 2D→3D supramolecular structure formed by π–π stacking interactions. Compound 5 possesses a 3D framework with a tfz-d net topology. Compounds 6 and 7 are constructed from the same auxiliary ligand and metal salt at the same temperature, but with different main ligands and exhibiting different topologies. Compound 6 presents a 3D 4,6-connected topological network with a Schläfli symbol of (3.44.6)(32.44.56.63), while compound 7 has a 3D topological network with a Schläfli symbol of (412.616). Magnetic analyses indicate that compounds 5 and 7 show weak antiferromagnetic interactions.

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“…The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies play a vital role in determining the chemical stability of the molecule. [ 48 ] The HOMO has an electron‐donating tendency, whereas LUMO is an electron acceptor. The energy difference between HOMO and LUMO are called band gap energy (△E = E LUMO − E HOMO ).…”

Section: Resultsmentioning

confidence: 99%

Metal–organic frameworks based on a benzimidazole flexible tetracarboxylic acid: Selective luminescence sensing Fe³⁺, magnetic behaviors, DFT calculations, and Hirshfeld surface analyses

Zhang

Xiong

et al. 2021

Applied Organom Chemis

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Four novel metal–organic frameworks constructed from benzimidazole flexible tetracarboxylic acid ligand, 1‐(3,5‐dicarboxylbenzyl)‐1H‐benzimidazole‐5,6‐dicarboxylic acid (H4L), have been prepared by a solvothermal method in the presence of N‐donor ancillary ligands (1,10‐phen = 1,10‐phenanthroline monohydrate, 4,4′‐bibp = 1,4‐di[pyridine‐4‐yl]benzene), namely, [Co2(L)(H2O)3]n (1), {[Cd2(L)(1,10‐phen)(H2O)]·2H2O}n (2), {[Co4(L)2(4,4′‐bibp)2(H2O)7]·4H2O}n (3), and {[Ni4(L)2(4,4′‐bibp)2(H2O)7]·4H2O}n (4). Complexes 1 and 2 show a 3D supramolecular structure and crystallize in monoclinic space group P21/c. Complexes 3 and 4 are isomorphous and crystallize in monoclinic space group Pn, and the respective metals exhibit a similar coordination environment. The H4L ligand behaved in different coordinated modes in Complexes 1–4, namely, μ6‐η1:η1:η1:η0:η1:η1:η1:η1:η1 in 1, μ6‐η1:η1:η1:η1:η1:η1:η2:η1:η1 in 2, there are two coordination modes (μ5‐η0:η1:η1:η0:η1:η1:η1:η0:η1 and μ5‐η1:η1:η1:η0:η1:η1:η1:η0:η1) in 3 and 4. Furthermore, photoluminescence and magnetic properties have been studied. The results indicate that Complexes 3 and 4 show strong antiferromagnetic and ferromagnetic coupling through M–O–C–O–M interactions, respectively. In particular, Complex 2 can sensitively and selectively detect Fe3+ in aqueous systems, and the limit of detection (LOD) values of Fe3+ is ∼0.19 mM.

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Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro[benzo[f]chromene-3,2′-indoline

Cited by 18 publications

References 32 publications

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

Seven new metal–organic frameworks assembled from semi-rigid polycarboxylate and auxiliary N-donor ligands: syntheses, structures and properties

Metal–organic frameworks based on a benzimidazole flexible tetracarboxylic acid: Selective luminescence sensing Fe³⁺, magnetic behaviors, DFT calculations, and Hirshfeld surface analyses

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Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro[benzo[f]chromene-3,2′-indoline

Cited by 18 publications

References 32 publications

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

A Structural Analysis of Spiropyran and Spirooxazine Compounds and Their Polymorphs

Seven new metal–organic frameworks assembled from semi-rigid polycarboxylate and auxiliary N-donor ligands: syntheses, structures and properties

Metal–organic frameworks based on a benzimidazole flexible tetracarboxylic acid: Selective luminescence sensing Fe3+, magnetic behaviors, DFT calculations, and Hirshfeld surface analyses

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Metal–organic frameworks based on a benzimidazole flexible tetracarboxylic acid: Selective luminescence sensing Fe³⁺, magnetic behaviors, DFT calculations, and Hirshfeld surface analyses