2008
DOI: 10.1002/chem.200801549
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Phosphorus‐Based Heteropentacenes: Efficiently Tunable Materials for Organic n‐Type Semiconductors

Abstract: Benzo-condensed dithieno[3,2-b:2',3'-d]phospholes have been synthesized that allow convenient tuning of properties that are essential for application as semiconductor materials in organic field-effect transistor (OFET) devices. The versatile reactivity of the trivalent phosphorus atom in these heteropentacenes provides access to a series of materials that show different photophysical properties, significantly different organization in the solid state, and distinctly different electrochemical properties that ca… Show more

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Cited by 143 publications
(84 citation statements)
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“…[3] The high practical value of MV 2+ is based on its pronounced electron-acceptor character and the change between intense colors (purple and orange) for the radical cation (MVC + ), and the neutral species (MV), respectively, that make the reduction event(s) easily detectable by optical spectroscopy or even the naked eye. [1a] In the context of systematic studies on phosphoruscontaining p-conjugated materials for organic electronics, our group [4] and others [5] could confirm the highly tunable, favorable electron-acceptor features that are attributable to the electronic nature of phosphorus. Recently we have extended our studies toward p-conjugated phospholes with pyridine units as integral part of the scaffold and were able to establish the highly functional nature, as well as the pronounced electron-accepting features of these systems, particularly for the phosphole oxides.…”
Section: Stefan Durben and Thomas Baumgartner*mentioning
confidence: 87%
“…[3] The high practical value of MV 2+ is based on its pronounced electron-acceptor character and the change between intense colors (purple and orange) for the radical cation (MVC + ), and the neutral species (MV), respectively, that make the reduction event(s) easily detectable by optical spectroscopy or even the naked eye. [1a] In the context of systematic studies on phosphoruscontaining p-conjugated materials for organic electronics, our group [4] and others [5] could confirm the highly tunable, favorable electron-acceptor features that are attributable to the electronic nature of phosphorus. Recently we have extended our studies toward p-conjugated phospholes with pyridine units as integral part of the scaffold and were able to establish the highly functional nature, as well as the pronounced electron-accepting features of these systems, particularly for the phosphole oxides.…”
Section: Stefan Durben and Thomas Baumgartner*mentioning
confidence: 87%
“…Compound 1 was subjected to a microwave‐assisted Knoevenagel condensation with malononitrile to afford 2 as a yellow microcrystalline solid (Scheme ). To tune the electronic properties, further derivatization of trivalent phosphorus in 2 was carried out . Treatment of 2 with elemental sulfur provided phosphine sulfide 3 (97 % yield), oxidation with H 2 O 2 gave phosphine oxide 4 (98 % yield), and methylation with methyl triflate furnished cation 5 (98 % yield).…”
Section: Methodsmentioning
confidence: 99%
“…To tune the electronic properties,f urtherd erivatization of trivalent phosphorus in 2 was carriedo ut. [14] Treatment of 2 with elemental sulfurp rovided phosphine sulfide 3 (97 %y ield), oxidation with H 2 O 2 gave phosphine oxide 4 (98 %y ield), and methylation with methyl triflatef urnished cation 5 (98 %y ield). All dicyanomethylenebridged compounds 2-5 were obtained as air-stable,c olorless solids which were soluble in common organic solvents.…”
mentioning
confidence: 97%
“…of MPHT ( Table 2, Entries 1 and 2). We were pleased to observe the quantitative formation of bis(3-bromobenzofuran) 4a and bis(3-bromobenzothiophene) 4b, which were used as starting materials for the synthesis of benzannulated phospholes, [15] dibenzothienopyrroles, [16] dithienosiloles, [17] and functionalized phenanthrenes [18] of physical interest. Unsymmetrical diyne 3c reacted cleanly with MPHT to afford expected heterocycle 4c, again with excellent yield (Table 2, Entry 3).…”
Section: Resultsmentioning
confidence: 99%