Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

Würthner, Frank; Stepanenko, Vladimir; Chen, Zhijian; Saha‐Möller, Chantu R.; Kocher, Nikolaus

doi:10.1021/jo048880d

Cited by 329 publications

(322 citation statements)

References 41 publications

(25 reference statements)

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“…For example Würthner et al [8] carried out a detailed study of bromination of PTCA and subsequent imidization, identifying issues relating to the regioselectivity of these reactions. Through a careful purification process they were able to isolate pure 1,7-dibromoperylene bisimide and then to proceed to synthesise 1,7-difunctionalised PDIs with a range of interesting properties.…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Interpreting the near-infrared reflectance of a series of perylene pigments

2013

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. and combination modes of fundamental IR vibrations appear to be more important in explaining the observed variations in NIR reflectance/absorbance. Aromatic groups lead to a small number of intense NIR bands, while alkyl groups generally lead to a greater number of less intense NIR bands. However, neighbouring group effects and/or a molecular dipole moment can substantially alter the intensity of these bands.

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Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Interpreting the near-infrared reflectance of a series of perylene pigments

2013

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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%

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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“…Compounds 1-5, 10-13 were prepared following the published procedures [10] [12]- [16]. All other chemicals are purchased from commercial source and used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

Photophysical Properties of Perylenetetracarboxylic Diimide Dimers with Slipped “Face-to-Face” Stacked Structure and Different Bay Substitutions

Qingdao¹

2016

MSCE

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A series of perylenetetracarboxylic diimides (PDIs) dimers with slipped "face-to-face" stacked structure and different substituents at the bay positions have been synthesized and the molecular structures are characterized by 1 H NMR, MALDI-TOF and elemental analysis. And different substituents at the bay positions of the PDI ring bring about various steric hindrances. These different steric hindrances have caused significant differences on the absorption and emission spectra. The correlation between the photophysical properties and the molecular structure is discussed.

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Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

Cited by 329 publications

References 41 publications

Interpreting the near-infrared reflectance of a series of perylene pigments

Interpreting the near-infrared reflectance of a series of perylene pigments

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

Photophysical Properties of Perylenetetracarboxylic Diimide Dimers with Slipped “Face-to-Face” Stacked Structure and Different Bay Substitutions

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