Liquid crystalline coronene derivatives

Rohr, U.; Kohl, Christopher; Müllen, Kläus; Craats, Anick van de; Warman, John M.

doi:10.1039/b009708j

Cited by 134 publications

(122 citation statements)

References 24 publications

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“…[13] Synthesis of 3: Compound 2 (1 g, 1.4 mmol), thiophenol (153 mg, 1.4 mmol) and potassium carbonate (128 mg, 1.4 mmol) were stirred in N-methylpyrrolidone (NMP, 80 mL) at room temperature. After 1.5 h, additional thiophenol (76 mg, 0.6 mmol) and potassium carbonate (128 mg, 1.4 mmol) were added to the reaction mixture, which was stirred at the same temperature for another 1.5 h. After cooling to room temperature, the reaction mixture was precipitated and washed with water and dried.…”

Section: Methodsmentioning

confidence: 99%

An Improved Perylene Sensitizer for Solar Cell Applications

et al. 2008

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Sunny side up: 1,6‐Dithiophenol‐substituted perylene organic sensitizer 1 was synthesized, and its photovoltaic properties in dye‐sensitized solar cells were assessed. When anchored onto TiO2 film, the dye exhibits an unprecedented incident monochromatic photon‐to‐current conversion efficiency of 87 % and yields a power conversion efficiency of 6.8 % under standard AM 1.5 solar conditions.

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Section: Methodsmentioning

confidence: 99%

An Improved Perylene Sensitizer for Solar Cell Applications

et al. 2008

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“…Synthesis of 5,11-dihexyl coronene-2,3,8,9-tetracarboxylic dianhydride has been reported previously. 21,[39][40][41] The electropolymerizable group, diphenylamine, was introduced in imide position by refluxing coronene dianhydride in quinoline for 24 hrs with 4-aminodiphenylamine. The structure of DCTD was confirmed by NMR, FT-IR and Mass spectrum analysis.…”

Section: Resultsmentioning

confidence: 99%

“…[14][15][16][17][18][19][20] Coronene derivatives have shown columnar discotic liquid-crystalline (LC) mesophases making them important candidates for organic electron transport materials due to extensive molecular ordering. [21][22] Coronene with an extended core size over perylene appears to have stronger intermolecular interactions leading to better charge-carrier mobility. Polymers based on perylene and naphthalene diimides have been synthesized and used as n-type semiconductors for organic field effect transistors.…”

Section: -13mentioning

confidence: 99%

Coronene Diimide Containing Redox Active Electrochromic Polymer Film via Electropolymerization of Diphenylamine End Groups

Paul¹,

Cammarata²

2018

J. Electrochem. Soc.

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A new monomer containing coronene diimide with diphenylamine end groups (DCTD) has been synthesized and polymer thin films were electropolymerized onto gold, glassy carbon and ITO electrode surfaces. The resulting polymers show a reversible 2e − oxidation of the diphenylbenzidine unit and reversible reductions of the aromatic diimide. AFM was used to characterize the polymer film morphology. The electronic and electrochromic properties of these films were evaluated for use in organic electronic applications. Research in the field of organic semiconducting polymers and their uses in electronics has grown rapidly in recent decades. [1][2][3][4][5][6] Considerable effort has been given to developing new polymers and investigating their properties. Our research group has focused on synthesizing new monomers containing a central redox active moiety flanked by two electropolymerizable functional groups and subsequently, studying the mechanism of this process as well as their optical and electronic properties. 7-13Perylene diimides have been reported as electron-transport materials with high electron mobility as well as having good chemical, thermal and photochemical stability. [14][15][16][17][18][19][20] Coronene derivatives have shown columnar discotic liquid-crystalline (LC) mesophases making them important candidates for organic electron transport materials due to extensive molecular ordering. [21][22] Coronene with an extended core size over perylene appears to have stronger intermolecular interactions leading to better charge-carrier mobility. Polymers based on perylene and naphthalene diimides have been synthesized and used as n-type semiconductors for organic field effect transistors. and carbazole. 35 p-phenoxyphenylamine and diphenylamine also can be electropolymerized at moderate oxidation potentials and make excellent end groups for electroactive monomers. 8 In our lab, diphenylamine functionalized at the imide position of perylene and naphthalene moieties have been synthesized and polymer films synthesized via electropolymerization.7-13 Spectroelectrochemistry of naphthalene diimide polymers show a solvent-dependent absorption energy band. 12We have also used electrochemical quartz crystal nanogravimetry to explore the mechanism of film formation and kinetics of ion incorporation into polymer films in case of perylene and naphthalene diimide polymer.11,13,36 Also these polymers exhibit robust, stable colors in different redox states making them promising candidates for electrochromic materials. 12,13Spin coating is the most used method to make thin films for fabricating optoelectronic devices. However, in the spin coating process, a * Electrochemical Society Member.z E-mail: scp0010@auburn.edu; cammavi@auburn.edu polymer has to be well soluble in a solvent. Due to this low solubility semiconducting polymers are difficult to fabricate into organic field effect transistor (OFET). Processes that result in highly self-organized thin films are desirable for better interchain pi-pi stacking. 37 It has been repo...

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“…Dibrominated PBIs 2a, c, d, f and tetrachlorinated PBIs 3a, c, d were synthesized according to the literature [17]. For the former compounds, mixtures of the 1,7-and 1,6-regioisomers in a ratio of about 9 : 1 were used.…”

Section: General Informationmentioning

confidence: 99%

“…The diflu- orinated perylene bisanhydride 1 was obtained by the reaction of dibrominated perylene bisanhydride with potassium fluoride at 160 • C in anhydrous sulfolane containing 18-crown-6 [16], while the dibrominated and tetrachlorinated precursor PBIs 2 and 3 were synthesized according to literature methods [17]. Imidization of difluorinated perylene bisanhydride 1 with amines 6a, b, d or e afforded the corresponding difluorinated perylene bisimides 4a, b, d and e in relatively lower yields (see Table 1).…”

Section: Synthesismentioning

confidence: 99%

Synthetic Routes to Core-fluorinated Perylene Bisimide Dyes and their Properties

Schmidt

Osswald

Könemann

et al. 2009

Zeitschrift Für Naturforschung B

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Numerous core-fluorinated perylene bisimide (PBI) dyes with various substituents at the imide positions have been synthesized by different methods. Core-difluorinated PBIs 4a-f are obtained by imidization of difluoro-substituted perylene bisanhydride 1 with appropriate primary amines or, alternatively, by nucleophilic halogen exchange reactions (Halex process) of the corresponding dibromosubstituted PBIs 2a-d,f with potassium fluoride. Core-tetrafluorinated PBIs 5a-c could also be synthesized by halogen exchange reactions of the respective tetrachlorinated PBIs 3a-c. In particular, core-fluorinated perylene bisimide pigments 4h, 5h containing hydrogen atoms in the imide positions could be obtained for the first time by deprotection of α-methylbenzyl-substituted precursors. Compared with core-unsubstituted perylene bisimides, these fluorinated dyes display hypsochromically shifted absorption and fluorescence spectra, and they exhibit fluorescence quantum yields up to unity, enabling bright yellow emission. The electrochemical properties of these electron-poor perylene bisimides have been studied. Furthermore, the packing features of a tetrafluorinated PBI derivative in the solid state have been discussed.

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Liquid crystalline coronene derivatives

Cited by 134 publications

References 24 publications

An Improved Perylene Sensitizer for Solar Cell Applications

An Improved Perylene Sensitizer for Solar Cell Applications

Coronene Diimide Containing Redox Active Electrochromic Polymer Film via Electropolymerization of Diphenylamine End Groups

Synthetic Routes to Core-fluorinated Perylene Bisimide Dyes and their Properties

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