Mixed stacking and stoichiometry in a π-molecular complex between fluorene and 1,3,5-trinitrobenzene

Mariezcurrena, R. A.; Russi, Silvia; Mombrú, Álvaro W.; Suescun, Leopoldo; Pardo, Helena; Tombesi, O. L.; Frontera, M. A.

doi:10.1107/s0108270199003662

Cited by 5 publications

(5 citation statements)

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“…As shown in the structure of the tri-crystal compound (Lynch et al, 1992b), which was prepared from the reaction of PABA with TNBA, the latter compound has a tendency to undergo facile decarboxylation (Coffey, 1977) often at a temperature lower than that of the usually employed refluxing conditions in 95% ethanol/water. The co-crystalline reaction products are stable 1:1 adducts involving 1,3,5-trinitrobenzene which associates with the companion molecule (Brown et al, 1964), skatole (Hanson, 1964), indole (Hanson, 1964), azulene (Hanson, 1965), acepleiadylene (Hanson, 1966), 2,4,6-tri(dimethylamino)-1,3,5-triazine (Williams & Wallwork, 1966), 1,3,5-triaminobenzene (Iwasaki & Saito, 1970), 8-hydroxyquinoline (oxine) (Castellano & Prout, 1971), pyrene (Prout & Tickle, 1973), azulene (Mariezcurrena et al,1999) and with indole-3-acetic acid (Lynch et al, 1991). Adducts with (2:1) stoichiometry are also known [with trans-azobenzene and N-benzylideneaniline (Bar & Bernstein, 1981)].…”

Section: Sup-1mentioning

confidence: 99%

“…The co-crystallized reaction products are stable 1:1 adducts involving 1,3,5-trinitrobenzene, which associates with the companion molecule through %±% stacking, together with weak NÐHÁ Á ÁO or CÐ HÁ Á ÁO hydrogen bonds between the stacks. Examples of this type of compound are the (1:1) adducts with anthracene (Brown et al, 1964), skatole (Hanson, 1964), indole (Hanson, 1964), azulene (Hanson, 1965;Mariezcurrena et al, 1999), acepleiadylene (Hanson, 1966), 2,4,6-tri(dimethylamino)-1,3,5-triazine (Williams & Wallwork, 1966), 1,3,5-triaminobenzene (Iwasaki & Saito, 1970), 8-hydroxyquinoline (oxine) (Castellano & Prout, 1971), pyrene (Prout & Tickle, 1973), and azulene (Mariezcurrena et al, 1999) and with indole-3acetic acid (Lynch et al, 1991). Adducts with (2:1) stoichiometry are also known [with trans-azobenzene and N-benzylideneaniline (Bar & Bernstein, 1981)].…”

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confidence: 99%

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The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

2002

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Section: Sup-1mentioning

confidence: 99%

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confidence: 99%

The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

2002

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“…We employed, as fluorene counterparts, tetracyanoethylene (TCNE in Figure 1), 1,2,4,5 tetracyanobenzene (TCNB) and 7,7,8,8-tetracyanoquinodimethane (TCNQ), all presenting D 2h symmetry. We were aware that the crystal structures of fluorene containing molecular complexes were disordered [4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

The Interpretation of the Short Range Disorder in the Fluorene-TCNE Crystal Structure

Croce

Arrais

Diana

et al. 2004

IJMS

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Abstract:The interpretation of the short-range static and/or dynamic disorder in a crystal structure from X-ray data is often a rather complex problem. Recently, we synthesized and characterized three co-crystalline complexes between fluorene, showing C 2v symmetry, and three electron withdrawing D 2h compounds, employing FTIR and Raman spectroscopy and single crystal X-ray diffraction techniques. The crystal structures of the complexes of fluorene with the three different electron withdrawing molecules are disordered in the solid state and only approximate structures were obtained by refinement of the single crystal data. Indeed, the fluorene moiety presents a very irregular geometry, showing for example C-C bonds ranging from 1.25Å to 1.75Å. Graphical inspection of the solved crystal structures indicates that the fluorene molecules in these co-crystalline complexes can assume two possible positions, both with 50% population. A two-step procedure to improve the disordered models is described. At first, the two possible ordered structures, with the fluorene molecule in only one of the two populated positions, are "separated" by molecular graphic techniques and then their geometry is fully optimized employing the periodic ab initio "CRYSTAL" code to obtain a chemically sensible model with reasonable distances and angles. The main aim of this communication is to demonstrate that ordered models can be obtained, starting from a disordered crystal structure, focusing our attention on the fluorene-TCNE molecular complex.

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“…10 A search in the Cambridge Structural Database (CSD) 11 of fluorene molecular complexes only gave three studies of the same complex between fluorene and 1,3,5-trinitrobenzene (with D 3h symmetry). [12][13][14] Besides, another paper is reported in literature, 15 dealing with a complex containing the fluorene molecular unit interacting with the D 2h electron-withdrawing 1,2,4,5-tetracyanobenzene. In both these structures, 14,15 the fluorene moieties present structural disorder.…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14] Besides, another paper is reported in literature, 15 dealing with a complex containing the fluorene molecular unit interacting with the D 2h electron-withdrawing 1,2,4,5-tetracyanobenzene. In both these structures, 14,15 the fluorene moieties present structural disorder.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural and spectroscopic study of the donor–acceptor complexes between fluorene and D_2hcyano molecular building blocks

et al. 2003

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Three solid molecular complexes of fluorene with electron-withdrawing tetracyanoethylene, 1,2,4,5tetracyanobenzene and 7,7,8,8-tetracyanoquinodimethane were synthesized. Single-crystal X-ray diffraction data elucidated the order-disorder aspects of the crystal structures ascribed to the different molecular symmetries of the employed building blocks. This hypothesis was confirmed by the structural and energetic results of ab initio periodic calculations. Donor-acceptor solid state interactions between molecular counterparts have been highlighted by electron and vibrational IR and Raman solid state spectroscopy, indicating a significant extent of electron density transfer from the fluorene unit towards the cyano-molecules. The experimental evidences of donor-acceptor interactions between molecular counterparts were compared to the lattice energies and solid state band-gaps, obtained by periodic calculations, and to the cluster HOMO-LUMO differences, obtained by isolated cluster calculations. A good agreement between spectral and theoretical data was found.

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Mixed stacking and stoichiometry in a π-molecular complex between fluorene and 1,3,5-trinitrobenzene

Cited by 5 publications

References 2 publications

The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

The Interpretation of the Short Range Disorder in the Fluorene-TCNE Crystal Structure

Synthesis, structural and spectroscopic study of the donor–acceptor complexes between fluorene and D_2hcyano molecular building blocks

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Mixed stacking and stoichiometry in a π-molecular complex between fluorene and 1,3,5-trinitrobenzene

Cited by 5 publications

References 2 publications

The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

The 1:1 adduct of 1,3,5-trinitrobenzene with 1,2,3,4-tetrahydroquinoline

The Interpretation of the Short Range Disorder in the Fluorene-TCNE Crystal Structure

Synthesis, structural and spectroscopic study of the donor–acceptor complexes between fluorene and D2hcyano molecular building blocks

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Synthesis, structural and spectroscopic study of the donor–acceptor complexes between fluorene and D_2hcyano molecular building blocks