Extended 2,5‐Diazaphosphole Oxides: Promising Electron‐Acceptor Building Blocks for π‐Conjugated Organic Materials

Linder, Thomas; Sutherland, Todd C.; Baumgartner, Thomas

doi:10.1002/chem.201000382

Cited by 21 publications

(20 citation statements)

References 46 publications

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“…One example in particular, utilized a similar backbone to 2,1,3-benzo[c]thiadiazole (BTD), resulting in 2,5-diazaphosphole oxide derivatives being easily synthesized from their corresponding phenanthrene and acenaphthene diimides (Scheme 6). 61 Although no devices were fabricated from these phospholes, electrochemical analysis showed that the phenanthrene based phosphole was easier to reduce than BTD (À0.95 V vs. À2.12 V; reference: Fc/Fc + ) indicating that more electronaccepting character could be introduced through the use of a diazaphosphole.…”

Section: Heterolesmentioning

confidence: 99%

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Organic n-type materials for charge transport and charge storage applications

Stolar

Baumgartner

2013

Phys. Chem. Chem. Phys.

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Conjugated materials have attracted much attention toward applications in organic electronics in recent years. These organic species offer many advantages as potential replacement for conventional materials (i.e., silicon and metals) in terms of cheap fabrication and environmentally benign devices. While p-type (electron-donating or hole-conducting) materials have been extensively reviewed and researched, their counterpart n-type (electron-accepting or electron-conducting) materials have seen much less popularity despite the greater need for improvement. In addition to developing efficient charge transport materials, it is equally important to provide a means of charge storage, where energy can be used on an on-demand basis. This perspective is focused on discussing a selection of representative n-type materials and the efforts toward improving their charge-transport efficiencies. Additionally, this perspective will also highlight recent organic materials for battery components and the efforts that have been made to improve their environmental appeal.

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Section: Heterolesmentioning

confidence: 99%

“…70 Scheme 6 Synthesis and structures of 2,5-diazaphosphole oxide derivatives from corresponding phenanthrene and acenaphthene diimides. 61 Fig. 14 Structure of functionalized NDIs and PDIs.…”

Section: Rylene Diimidesmentioning

confidence: 99%

Organic n-type materials for charge transport and charge storage applications

Stolar

Baumgartner

2013

Phys. Chem. Chem. Phys.

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“…The chemistry was extended to other main group diazole heterocycles, such as the π-extended phosphadiazole 12 , which was produced in 79% yield (by 1 H NMR spectroscopy) upon treatment of titanacycle 6 with POCl 2 Ph. Unfortunately, compound 12 could not be isolated due to the difficulty in separating the Cp 2 TiCl 2 byproduct, which was complicated by the hydrolytic lability of the P–N bond in this compound.…”

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confidence: 99%

Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons

et al. 2018

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A general synthetic strategy for the construction of large, nitrogen-containing polycyclic aromatic hydrocarbons (PAHs) is reported. The strategy involves two key steps: (1) a titanocene-mediated reductive cyclization of an oligo(dinitrile) precursor to form a PAH appended with di(aza)titanacyclopentadiene functionality; (2) a divergent titanocene transfer reaction, which allows final-step installation of one or more o-quinone, diazole, or pyrazine units into the PAH framework. The new methodology enables rational, late-stage control of HOMO and LUMO energy levels and thus photophysical and electrochemical properties, as revealed by UV/vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. More generally, this contribution presents the first productive use of di(aza)metallacyclopentadiene intermediates in organic synthesis, including the first formal [2 + 2 + 2] reaction to form a pyrazine ring.

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“…77 A number of other phosphole compounds with extended p-systems have also been examined as potential p-conjugated materials with interesting optical properties. [78][79][80][81][82] The incorporation of phosphorus-containing groups into porphrinoid compounds has been shown to give rise to the first example of a structurally-characterised Mo¨bius antiaromatic system. 83 A related series of compounds based on octaphyrin have also been reported.…”

Section: Phosphorusmentioning

confidence: 99%