Aniline-based bis(enamines) as new amorphous molecular charge transport materials

Puodziukynaite, Egle; Burbulis, E.; Gražulevičius, Juozas V.; Jankauskas, Vygintas; Undzenas, A.; Linonis, Vitas

doi:10.1016/j.synthmet.2007.07.009

Cited by 5 publications

(3 citation statements)

References 8 publications

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“…Biphenyl derivatives BE1 , BE2 , BE3 and their analogue BE4 were synthesized via facile one-step camphorsulfonic acid (CSA) catalyzed diphenylacetaldehyde condensation reaction with the corresponding aromatic diamines ( scheme 1 ) [ 25 ]. Although all four target compounds were isolated in similar yields, it still can be noticed that the presence of a stronger electron-donating group in the benzene ring increases reactivity of aromatic diamine and therefore a higher yield of BE3 is obtained.…”

Section: Resultsmentioning

confidence: 99%

“…Thermal stability of biphenyl enamines was measured using thermogravimetric analysis (TGA); the results are listed in table 1 . For comparison, two known biphenyl derivatives 4,4′-oxybis[ N , N -bis(2,2-diphenylethenyl)aniline] (OBDA) [ 25 ] and N 4 , N 4 , N 4 ′, N 4 ′-tetrakis(2,2-diphenylethenyl)–2,2′-dimethyl[1,1′-biphenyl]-4,4′-diamine (H3) ( figure 1 ) [ 24 ] are also added to table 1 .…”

Section: Resultsmentioning

confidence: 99%

“…Thermal stability of biphenyl enamines was measured using thermogravimetric analysis (TGA); the results are listed in table 1. For comparison, two known biphenyl derivatives 4,4 0 -oxybis[N,N-bis(2,2-diphenylethenyl)aniline] (OBDA) [25] and 1) [24] are also added to table 1. royalsocietypublishing.org/journal/rsos R. Soc.…”

Section: Thermal Propertiesmentioning

confidence: 99%

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Investigation of biphenyl enamines for applications as p-type semiconductors

et al. 2023

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Due to the ease of synthesis and the ability to easily tune properties, organic semiconductors are widely researched and used in many optoelectronic applications. Requirements such as thermal stability, appropriate energy levels and charge-carrier mobility have to be met in order to consider the suitability of an organic semiconductor for a specific application. Balancing of said properties is not a trivial task; often one characteristic is sacrificed to improve the other and therefore a search for well-balanced materials is necessary. Herein, seven new charge-transporting biphenyl-based enamine molecules are reported. The new materials were synthesized using a simple one-step reaction without the use of expensive transition metal catalysts. It was observed that subtle variations in the structure lead to notable changes in the properties. Materials exhibited high thermal stability and relatively high carrier drift mobility, reaching 2 × 10 −2 cm 2 V −1 s −1 (for BE3 ) at strong electric fields. Based on the results, three materials show the potential to be applied in organic light emitting diodes and solar cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Investigation of biphenyl enamines for applications as p-type semiconductors

et al. 2023

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Carbazole-based bis(enamines) as effective charge-transporting amorphous molecular materials

et al. 2008

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Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

Tahara¹,

Miyamoto²,

Aoto³

et al. 2015

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The appropriate design of a ligand (L) in IrCl(CO)(L)2 (4) realized the efficient synthesis of π-conjugated enamines possessing hole-transport properties. The iridium complex with electron-withdrawing phosphorus ligands catalyzed the hydrosilylation of amides to the corresponding silylhemiaminals, which were transformed to the enamines by heat or by treatment with acids. High catalytic efficiency (TON > 10,000) was achieved, which made it possible for the residual iridium in the enamine product to be below 20 ppb.

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Aniline-based bis(enamines) as new amorphous molecular charge transport materials

Cited by 5 publications

References 8 publications

Investigation of biphenyl enamines for applications as p-type semiconductors

Investigation of biphenyl enamines for applications as p-type semiconductors

Carbazole-based bis(enamines) as effective charge-transporting amorphous molecular materials

Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

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