Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

Holzapfel, Marco; Lambert, Christoph; Selinka, Carola; Stalke, Dietmar

doi:10.1039/b204392k

Cited by 35 publications

(36 citation statements)

References 42 publications

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“…[216] As shown in Scheme 41, the distinctive characteristics of this class of MV compounds are the large reorganization energy, which to some extent results from the planarization of the phenazine moiety upon oxidation, but is mainly due to changes in the CÀC and CÀN bonds, as shown by X-ray crystal data and density functional computations. [216] The optical band shape analysis of 114 + -117 + shows a decrease in the electronic communication with increasing spacer length, whereupon the values for V are on the same order of magnitude as for analogous bis(triarylamine) radical cations with identical spacer moieties (3 + , 4 + , 63 + , and 73 a + ). Unfortunately, optical analysis of 116 + was not possible due to strong overlap of the IV-CT band with higher energy transitions.…”

Section: Mixed-valence Compoundsmentioning

confidence: 99%

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

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495

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Mixed-valence (MV) compounds are excellent model systems for the investigation of basic electron-transfer (ET) or charge-transfer (CT) phenomena. These issues are important in complex biophysical processes such as photosynthesis as well as in artificial electronic devices that are based on organic conjugated materials. Organic MV compounds are effective hole-transporting materials in organic light emitting diodes (OLEDs), solar cells, and photochromic windows. However, the importance of organic mixed-valence chemistry should not be seen in terms of the direct applicability of these species but the wealth of knowledge about ET phenomena that has been gained through their study. The great variety of organic redox centers and spacer moieties that may be combined in MV systems as well as the ongoing refinement of ET theories and methods of investigation prompted enormous interest in organic MV compounds in the last decades and show the huge potential of this class of compounds. The goal of this Review is to give an overview of the last decade in organic mixed valence chemistry and to elucidate its impact on modern functional materials chemistry.

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Section: Mixed-valence Compoundsmentioning

confidence: 99%

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

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510

495

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“…This value could be compared with the corresponding angle reported for N,Ndihydrodimethylphenazine (1448). 9 The corresponding dipropionylated compound, 6b, could similarly be prepared (43%) using propionic anhydride without any co-formation of 2d. When 2b was treated with zinc in boiling propionic anhydride (neat) for 20 h even the tripropionylated compound 6c could be obtained.…”

Section: Resultsmentioning

confidence: 99%

Reduction of indolo[2,3-b]quinoxalines

2005

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“…Compound 12 was synthesized by a palladium-catalyzed Sonogashira reaction of 11 and trimethylsilylacetylene. The protecting trimethylsilyl group was removed with TBAF to obtain compound 13 [41]. A Sonogashira reaction of 13 with 14 yielded SEMA4 in 12% yield.…”

Section: Synthesis Of Raman Reporter Moleculesmentioning

confidence: 99%

Design and synthesis of Raman reporter molecules for tissue imaging by immuno‐SERS microscopy

Schütz

Müller

Salehi

et al. 2011

Journal of Biophotonics

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The design and synthesis of Raman reporter molecules comprising olefin or alkyne moieties with strong and characteristic vibrational Raman bands is presented. Chemisorption onto the surface of colloidal Au/Ag shells yields a self-assembled monolayer. Hydrophilic stabilization of such SERS labels can be achieved by short terminal ethylene glycol units attached to the Raman reporter. Encapsulation by silica with subsequent functionalization of the glass surface allows the conjugation to biomolecules such as antibodies. We demonstrate the use of SERS-labeled antibodies for tissue imaging of the tumor suppressor p63 in prostate biopsies.

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Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

Cited by 35 publications

References 42 publications

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Reduction of indolo[2,3-b]quinoxalines

Design and synthesis of Raman reporter molecules for tissue imaging by immuno‐SERS microscopy

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