Elementorganische Verbindungen mit o-Phenylenresten, XXVIII [1] Charge-transfer-Komplexe von 2,3,7,8-Tetraalkoxy-chalkogenanthrenen mit 7,7,8,8-Tetracyan-2,3,5,6-tetrafluor-chinodimethan / Organometalloidal Compounds with o-Phenylene Substituents, Part XXVIII [1] Charge-Transfer Complexes of 2,3,7,8-Tetraalkoxy-chalcogenanthrenes wjth 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoro-quinodimethane

Friederichs, S.; Kudnig, J.; Klar, G.

doi:10.1515/znb-1996-0913

Cited by 3 publications

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“…The projection orthogonal to the mean plane of picene (Figure ) shows the slipped orientation of molecules in the stacks, with the average distance between the F 4 -TCNQ molecule and the picene plane being equal to 3.25 Å, which is the first evidence of the comparatively strong interaction between the donor and acceptor molecules. In general, the interplanar mean plane distances after charge transfer between F 4 -TCNQ acceptor and donor molecules containing different aromatic fragments vary from 3.25 to 3.29 Å in compounds with cyclophane derivatives containing a benzene fragment, − from 3.31 to 3.35 Å in compounds with 5,10-dithia- and -diselenanthrene derivatives, and to 3.36 Å in the compound with trans -stilbene …”

Section: Resultsmentioning

confidence: 99%

Crystal Growth, Structure, and Transport Properties of the Charge-Transfer Salt Picene/2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Mahns

Kataeva

Islamov

et al. 2014

Crystal Growth & Design

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Single crystals of the charge-transfer salt picene/2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane have been grown using physical vapor transport. The crystal structure was determined using single-crystal X-ray diffraction. It was found that the crystals grow in a 1:1 molecular ratio and adopt a monoclinic structure with alternate stacking. Both Xray data and Raman measurements show that the grown crystals are of good quality. From structure and infrared data, the charge transfer between acceptor and donor molecules was estimated to be approximately 0.14−0.19 electron. Transport measurements indicate a nonmetallic ground state with an activation energy of 0.6 eV. The supporting density functional theory calculations on molecular model systems as well as on crystalline structures confirm the amount of charge transfer and provide first insights into the electronic structure of the new material.

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Section: Resultsmentioning

confidence: 99%

Crystal Growth, Structure, and Transport Properties of the Charge-Transfer Salt Picene/2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Mahns

Kataeva

Islamov

et al. 2014

Crystal Growth & Design

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“…Thianthrenes participating in charge-transfer complexes flatten even further, and a 0° dihedral angle (complete planarity) was twice reported. 12,13 In 12, the distances from the outer edge of the flaps to the SS creases are 3.92-3.93 Å. A flattening of the thianthrene portions of the flaps by just 5° would swing the outer carbon atoms outwards by 0.35 Å, enough to allow much better docking.…”

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“…1 H NMR (400 MHz, CDCl 3 ): d = 7.89 (s, 5 H), 3.12 (t, J = 7.2 Hz, 10 H), 1.79 (m, 10 H), 1.09 (t, J = 7.2 Hz, 15 H). 13 1,3,5,7,9-Pentakis(1-dodecylthio)corannulene (6). 1,3,5,7,9-Pentachlorocorannulene 1 (2, 20 mg, 0.04 mmol) and sodium 1-dodecanethiolate (106 mg, 0.47 mmol), prepared as above from 1-dodecanethiol and sodium in absolute EtOH, were stirred in 1.0 mL of 1,3-dimethylimidazolidin-2-one (DMEU) at r.t. under nitrogen for 5 d. During the reaction period, the color of the mixture changed from reddish brown to deep green.…”

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Corannulene Polysulfides: Molecular Bowls with Multiple Arms and Flaps

Bancu¹,

Amarjit²,

Cheng³

et al. 2004

Synlett

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Nucleophilic aromatic substitution of all the chlorine atoms in 1,3,5,7,9-pentachlorocorannulene and in decachlorocorannulene by sodium alkanethiolates gives 1,3,5,7,9-pentakis(1-alkylthio)corannulenes, C 20 H 5 (SR) 5 , and decakis(1-alkylthio)corannulenes, C 20 (SR) 10 , respectively, with arms of varying lengths attached around the perimeter (R = n-propyl, n-hexyl, and ndodecyl). The corresponding reaction of decachlorocorannulene with ortho-C 6 H 4 (SNa) 2 gives pentakis(1,4-benzodithiino)corannulene, a molecular bowl with 6 Å flaps on all five sides. Such compounds represent attractive candidates for the formation of discotic liquid crystals and/or supramolecular complexes with fullerenes and other convex guests.Our discovery that the chlorination of corannulene (1) with I-Cl at room temperature gives pentachlorocorannulene with surprisingly high selectivity for the 1,3,5,7,9-isomer 2 1 opened the door to a new family of molecular bowls that bear substituents around the entire perimeter ( Figure 1). 1-3 Figure 1Corannulene (C 20 H 10 ) and several 1,3,5,7,9-pentakis-X derivatives Within this new family of compounds, the pentakis(SAr) derivatives 3 and 4 were found to be well-suited as hosts for the complexation of C 60 (K assoc = 10 2 -10 3 M -1 ). 3 The choice of aryl groups in these fullerene hosts was strongly influenced by the fact that C 60 exhibits good solubility in both anisole and methylnaphthalene, 4 and it is tempting to envision the arms of 3 and 4 embracing the C 60 in these complexes (Figure 2). This view is reinforced by the failure of unsubstituted corannulene (1) to show any evidence for binding to C 60 . 5Notwithstanding this appealing picture, the question remains whether or not 'intramolecular solvation' by the five tethered arenes represents the primary factor responsible for the superior binding ability of the pentakis(SAr) derivatives 3 and 4. The five sulfur atoms attached around the perimeter of the geodesic polyarene core in 3 and 4 must certainly render their concave surfaces more electron rich and more polarizable than the interior surface of the parent corannulene, and that could be the dominant factor. Figure 2 Hypothetical structure for the 1:1 complex C 60 ·3, with the five arms of 3 embracing the C 60To probe this issue, we have synthesized the 1,3,5,7,9-pentakis(S-CH 2 CH 2 CH 3 ) derivative 5, which lacks electron-rich p-systems on the arms but retains the geodesic polyarene core and the five attached sulfur atoms. As in our syntheses of 3 and 4, 3 the conversion of 2 to 5 could be effected under quite mild conditions. Thus, stirring 1,3,5,7,9-pentachlorocorannulene (2) with sodium 1-propanethiolate in 1,3-dimethylimidazolidin-2-one (dimethylethanourea = DMEU) at room temperature for 3 days gave 1,3,5,7,9-pentakis(1-propylthio)corannulene (5) in 38% yield, after purification. In the same manner, a 1,3,5,7,9-pentakis(1-alkylthio)corannulene with much longer arms 6 was also prepared from 2. 6 Starting from decachlorocorannulene (7), 7 the same reaction was used to make a fami...

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ChemInform Abstract: Organometalloidal Compounds with o‐Phenylene Substituents. Part 28. Charge‐Transfer Complexes of 2,3,7,8‐Tetraalkoxy‐chalcogenanthrenes with 7,7,8,8‐Tetracyano‐2,3,5,6‐tetrafluoro‐quinodimethane.

1997

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1997organo-selenium compounds, nonmetal heterocycles organo-selenium compounds, nonmetal heterocycles S 0137 -241Organometalloidal Compounds with o-Phenylene Substituents. Part 28.Charge-Transfer Complexes of 2,3,7,8-Tetraalkoxychalcogenanthrenes with 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane.-Isostructural 1:1 CT complexes are formed between (I) and the title quinodimethane (II), which show in their columnar crystal structures alternating donor and acceptor molecules. The interactions in the compounds are explained by MNDO calculations.-(FRIEDERICHS, S.; KUDNIG, J.; KLAR, G.

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Cited by 3 publications

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Crystal Growth, Structure, and Transport Properties of the Charge-Transfer Salt Picene/2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Crystal Growth, Structure, and Transport Properties of the Charge-Transfer Salt Picene/2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Corannulene Polysulfides: Molecular Bowls with Multiple Arms and Flaps

ChemInform Abstract: Organometalloidal Compounds with o‐Phenylene Substituents. Part 28. Charge‐Transfer Complexes of 2,3,7,8‐Tetraalkoxy‐chalcogenanthrenes with 7,7,8,8‐Tetracyano‐2,3,5,6‐tetrafluoro‐quinodimethane.

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