ChemInform Abstract: Synthesis, Photooxidation and Mass Spectra of 5,6,11,12‐Tetrachlorotetracene.

Balodis, K. A.; Medne, R. S.; Neiland, O. Ya.; Kozlova, L. М.; Klyavinya, Z. P.; Mazheika, I. B.; Gaukhman, A.

doi:10.1002/chin.198611192

Cited by 3 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tetrachlorotetracene is known to react with oxygen and give peroxide 5, which can continue to undergo further and irreversible decomposition to form quinone 6 (Scheme 2). 7 Our proposed degradation pathway is similar to the reaction of rubrene 1 with oxygen to form peroxide 7, although rubrene 1 can be regenerated from the peroxide upon heating or decreasing pressure. 18 To confirm that quinone formation via reaction with oxygen was the cause of the surface degradation rather than other pathways (such as acene dimerization), we sought to identify the formation of 6 in solid samples of 2.…”

Section: Resultsmentioning

confidence: 76%

“…Material prepared by this method was typically higher in quality as judged by 1 H NMR and thin-layer chromatography compared to material available at relatively high price from typical fine chemical vendors (Sigma-Aldrich, 1 g, $59.10). Chlorination of 3 using phosphorus oxychloride and phosphorus pentachloride (84%), followed by dechlorination with sodium iodide in DMF (79%), proceeded largely according to the established procedure, 7 with only minor modifications to improve yield and purity.…”

Section: Resultsmentioning

confidence: 99%

“…We have modified the known synthetic route to tetrachlorotetracene 2 to be amenable to multigram scale (Scheme ). Our synthesis begins with a Friedel−Crafts acylation of phthaloyl chloride and 1,4-dihydroxynaphthalene.…”

Section: Resultsmentioning

confidence: 99%

“…6 To better understand the exceptional behavior of rubrene single crystal devices, we are undertaking the synthesis and characterization of rubrene and its analogs such as tetrachlorotetracene 2. Tetrachlorotetracene was first synthesized in 1985, 7 and there was an initial study of its electronic properties. 8 In this paper, we describe a synthesis of tetrachlorotetracene 2, crystal structures of 2 and its synthetic precursor dihydroxytetracenedione 3, and FET properties and atomic force microscopy (AFM) measurements of 2.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene

et al. 2009

View full text Add to dashboard Cite

Tetrachlorotetracene is an organic semiconductor and has possible applications in flexible organic devices. We have synthesized tetrachlorotetracene in multigram quantities in three steps from commercially available substances, with an overall yield of 52%. X-ray crystallographic analysis of tetrachlorotetracene and its precursor dihydroxytetracenedione showed similar packing structures, with better pitch stacking and roll stacking angles observed for tetrachlorotetracene. Single crystals of tetrachlorotetracene are semiconducting with field effect hole mobility values up to 0.2 cm2/V s. The hole mobility has been measured in the temperature range of 230−290 K, and Arrhenius behavior was observed, with an activation energy of nearly 200 meV. Such a large activation energy suggests significant carrier trapping. Air stability studies showed slow degradation of the crystal surface by atomic force microscopy, along with degradation of the semiconducting properties. We hypothesize that the instability of tetrachlorotetracene to air is the result of decomposition to a quinone species, a degradation previously observed in solution phase studies.

show abstract

Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene

et al. 2009

View full text Add to dashboard Cite

show abstract

“…We prepared new rubrene derivatives 1h – n and 1p from dichloroquinone 2 following our previously reported route (Table ). − Rubrene 1o required an alternate synthetic route, which is described in the discussion section . Experimental procedures and tabulated characterization data for all new compounds are in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Ogden

Ghosh

Bruzek

et al. 2017

Crystal Growth & Design

View full text Add to dashboard Cite

Through a close examination of the intermolecular interactions of rubrene (1a) and select derivatives (1b− 1p), a clearer understanding of why certain fluorinated rubrene derivatives pack with planar tetracene backbones has been achieved. In this study we synthesized, crystallized, and determined the packing structure of new rubrene derivatives (1h−p). Previously, we proposed that introducing electronwithdrawing CF 3 substituents induced planarity by reducing intramolecular repulsion between the peripheral aryl groups (1e−g). However, we found that in most cases, further increasing the fluorine content of rubrene lead to twisted tetracene backbones in the solid state. To understand how rubrene (1a) and its derivatives (1b−p) pack in the solid state, we (re)examined the crystal structures through a systematic study of the close contacts. We found that planar tetracene cores occur when close contacts organize to produce an S symmetry element about a given rubrene molecule. We report the first instance of rubrene derivatives (1l and 1n) that pack in a two-dimensional brick motif. The prospects for new rubrene derivatives in semiconductors were estimated by calculating the reorganization energies of the monomers and transfer integrals of the dimers we observed. Our work allows for the rational design and improved crystal engineering of new rubrene derivatives.

show abstract

Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties

et al. 2013

View full text Add to dashboard Cite

Correlations among the molecular structure, crystal structure, electronic structure, and charge-carrier transport phenomena have been derived from six congeners (2–7) of rubrene (1). The congeners were synthesized via a three-step route from known 6,11-dichloro-5,12-tetracenedione. After crystallization, their packing structures were solved using single-crystal X-ray diffraction. Rubrenes 5–7 maintain the orthorhombic features of the parent rubrene (1) in their solid-state packing structures. Control of the packing structure in 5–7 provided the first series of systematically manipulated rubrenes that preserve the π-stacking motif of 1. Density functional theory calculations were performed at the B3LYP/6-31G(d,p) level of theory to evaluate the geometric and electronic structure of each derivative and reveal that key properties of rubrene (1) have been maintained. Intermolecular electronic couplings (transfer integrals) were calculated for each derivative to determine the propensity for charge-carrier transport. For rubrenes 5–7, evaluations of the transfer integrals and periodic electronic structures suggest these derivatives should exhibit transport characteristics equivalent to, or in some cases improved on, those of the parent rubrene (1), as well as the potential for ambipolar behavior. Single-crystal field-effect transistors were fabricated for 5–7, and these derivatives show ambipolar transport as predicted. Although device architecture has yet to be fully optimized, maximum hole (electron) mobilities of 1.54 (0.28) cm2 V–1 s–1 were measured for rubrene 5. This work lays a foundation to improve our understanding of charge-carrier transport phenomena in organic single-crystal semiconductors through the correlation of designed molecular and crystallographic changes to electronic and transport properties.

show abstract

ChemInform Abstract: Synthesis, Photooxidation and Mass Spectra of 5,6,11,12‐Tetrachlorotetracene.

Abstract: Nach einem abgewandelten Verfahren wird die Titelverbindung (I‐II) mit höherer Ausb. und in größerer Reinheit erhalten.

Cited by 3 publications

References 0 publications

Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene

Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene

Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties

Contact Info

Product

Resources

About