SELFSTACKING SYSTEMS, PART 6.<sup>1</sup>HOST LATTICE FUNCTION OF 2,3,8,9-TETRAMETHOXYDIBENZO[<i>c,e</i>][1,2]-DICHALCOGENINS IN THEIR ELECTRICALLY CONDUCTING IODINE COMPLEXES

Behrens, Joachim; Hinrichs, W.; Link, T.; Schiffling, C.; Klar, G.

doi:10.1080/10426509508042522

Cited by 15 publications

(11 citation statements)

References 18 publications

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“…In order to investigate intermolecular coupling, 2,2¢-diiodo-4,4¢,5,5¢-tetramethoxybiphenyl (5) 14 was initially employed as the starting material. Halogen-lithium exchange occurred smoothly at -78°C in THF to produce the dilithio derivative, which underwent transmetallation 15 14,[16][17][18] was also investigated for the synthesis of 8. A similar experiment was carried out using ZnBr 2 and the compound 8 was isolated in 52% yield.…”

Section: Methodsmentioning

confidence: 99%

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Kabir

Iyoda

2000

Synthesis

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The intramolecular coupling of benzoannelated zincacyclopentadiene using CuCl 2 produced 1,8-dibromobiphenylene selectively in a good yield. On the contrary, the intermolecular coupling of zincacyclopentadiene produced 2,3,6,7,10,11,14,15-octamethoxytetraphenylene selectively in a synthetically reasonable yield under different reaction conditions. The reactions of 2,2¢-dilithio-4,4¢,5,5¢-tetramethoxybiphenyl and 2,2¢-dilithio-4,4¢,5,5¢-tetrakis(tert-butyldimethylsilyloxy)biphenyl with CuCl 2 in THF unexpectedly produced the corresponding tetraphenylene derivatives, instead of the desired biphenylene derivatives. Octamethoxytetraphenylene was used to synthesize octaacetoxytetraphenylene in a quantitative yield either directly or through octahydroxytetraphenylene.

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Section: Methodsmentioning

confidence: 99%

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Kabir

Iyoda

2000

Synthesis

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“…1, Vb). The first one of these two polymorphic forms of the tetramethoxy compound was reported long ago; the second one has been obtained in the present work, via a synthetic route of our own, since no details are given in the original report by Behrens et al (1995). Both structures share the P2 1 /c space group, with similar volumes (Table 1).…”

Section: Structures (Ii)mentioning

confidence: 74%

“…In what follows we provide a brief description of the crystal and molecular structures/interactions of (I), (II), (III) (Zelcer et al, 2013), (IV), (Va) (Behrens et al, 1995) and (Vb) (see Table 1 and Fig. 1).…”

Section: Crystal Structures and Aim Analysismentioning

confidence: 99%

“…Rather surprisingly, in spite of their relevance as precursors for soft materials, no systematic structural studies have been carried out on OR 3,3 0 ,4,4 0 -biphenyls. Indeed, there are only two reported structures of such compounds: a twisted short chain derivative (Behrens et al, 1995) and a mixed long chain/ acetoxy derivative which some of us reported in the context of biphenyls as precursors for liquid crystals such as triphenylenes (Zelcer et al, 2013). The rigorous planarity of the tworing system in 3,3 0 -di(hexyloxy)-4,4 0 -di(acetoxy)biphenyl was not further analyzed, as that communication focused on the versatility of our synthetic scheme; this was within the context of the so-called biphenyl route (Boden et al, 1994) among the rational synthetic pathways (Pé rez & Guitiá n, 2004) to triphenylenes to yield functionalized triphenylenes able to be incorporated in extended materials.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and crystallographic, spectroscopic and computational characterization of 3,3′,4,4′-substituted biphenyls: effects of ORsubstituents on the intra-ring torsion angle

Vadra

Suárez

Slep

et al. 2020

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Presented here are the synthesis, characterization and study (using single crystal X-ray diffraction, Raman scattering, quantum mechanics calculations) of the structures of a series of biphenyls substituted in positions 3, 3 0 , 4 and 4 0 with a variety of R (R = methyl, acetyl, hexyl) groups connected to the biphenyl core through oxygen atoms. The molecular conformation, particularly the torsion angle between aromatic rings has been extensively studied both in the solid as well as in the liquid state. The results show that the compounds appearing as rigorously planar in the solid present instead a twisted conformation in the melt. The solid versus melt issue strongly suggests that the reasons for planarity are to be found in the packing restraints. A 'rule of thumb' is suggested for the design of biphenyls with different molecular conformations, based on the selection of the OR substituent. research papers Acta Cryst. (2020). B76, 366-377 N. Vadra et al. OR substituents effects on the torsion angle of biphenyls 367 † We report here the total sum of the interactions between chains and C-HÁ Á Á (in brackets the numbers of BCP involved in each compound), which individual values range between 0.15-0.55 (for ) and 0.05-0.17 (for r 2 ). See Fig. SI2.

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“…Black and white molecules correspond to stacks of R and S enantiomers of DTB. Circles represent iodine chains parallel to the crystallographic b axis …”

Section: Introductionmentioning

confidence: 99%

Intercalation and Deintercalation of Iodine into 2,3,8,9-Tetramethoxydibenzo[c,e][1,2]- dithiin: A Detailed Mechanistic Study of a Gas−Solid Reaction Leading to an Organic Conductor

et al. 1997

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2,3,8,9-Tetramethoxydibenzo[c,e][1,2]dithiin (“dithiobiphenyl” = “DTB”) forms a host lattice for iodine. Electron transfer from DTB to iodine leads to the formation of an organic semiconductor with the approximate formula of DTB·I1.16. This host−guest complex can be prepared either by cocrystallization of both compounds from solution or by treating solid DTB with gaseous iodine. Upon heating, iodine is released again. Both intercalation and deintercalation were studied with physicochemical methods, among them thermal analysis, electron paramagnetic resonance (EPR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), and thermomicroscopy.

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SELFSTACKING SYSTEMS, PART 6.¹HOST LATTICE FUNCTION OF 2,3,8,9-TETRAMETHOXYDIBENZO[c,e][1,2]-DICHALCOGENINS IN THEIR ELECTRICALLY CONDUCTING IODINE COMPLEXES

Cited by 15 publications

References 18 publications

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Synthesis and crystallographic, spectroscopic and computational characterization of 3,3′,4,4′-substituted biphenyls: effects of ORsubstituents on the intra-ring torsion angle

Intercalation and Deintercalation of Iodine into 2,3,8,9-Tetramethoxydibenzo[c,e][1,2]- dithiin: A Detailed Mechanistic Study of a Gas−Solid Reaction Leading to an Organic Conductor

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SELFSTACKING SYSTEMS, PART 6.1HOST LATTICE FUNCTION OF 2,3,8,9-TETRAMETHOXYDIBENZO[c,e][1,2]-DICHALCOGENINS IN THEIR ELECTRICALLY CONDUCTING IODINE COMPLEXES

Cited by 15 publications

References 18 publications

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Synthesis and crystallographic, spectroscopic and computational characterization of 3,3′,4,4′-substituted biphenyls: effects of ORsubstituents on the intra-ring torsion angle

Intercalation and Deintercalation of Iodine into 2,3,8,9-Tetramethoxydibenzo[c,e][1,2]- dithiin: A Detailed Mechanistic Study of a Gas−Solid Reaction Leading to an Organic Conductor

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SELFSTACKING SYSTEMS, PART 6.¹HOST LATTICE FUNCTION OF 2,3,8,9-TETRAMETHOXYDIBENZO[c,e][1,2]-DICHALCOGENINS IN THEIR ELECTRICALLY CONDUCTING IODINE COMPLEXES