Hole-transporting phenothiazine-based hydrazones with reactive vinylbenzyl groups

Laurinaviciute, Rasa; Ostrauskaitė, Jolita; Skuodis, Eigirdas; Gražulevičius, Juozas V.; Jankauskas, Vygintas

doi:10.1016/j.synthmet.2014.03.009

Cited by 8 publications

(4 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 −6 cm 2 V −1 s −1 ). These low mobility values are comparable to those reported in the literature for other solution-deposited3233343569 and thermally evaporated70 phenothiazine derivatives. To the best of our knowledge, the mobility of O-1 is the highest reported for phenothiazine-based small molecules, without complexation with iodine.…”

Section: Resultssupporting

confidence: 89%

Crystallisation-enhanced bulk hole mobility in phenothiazine-based organic semiconductors

Shinde

Salunke

Candeias

et al. 2017

Sci Rep

View full text Add to dashboard Cite

A series of three novel donor-acceptor systems based on C(3)-malononitrile-substituted phenothiazines was synthesised in good overall yields and their thermal, spectroscopic, and electrochemical properties were characterised. The compounds were prepared through a sequence of Ullmann-coupling, Vilsmeier-Haack formylation and Knoevenagel-condensation, followed by Suzuki-coupling reactions for introduction of aryl substitutents at C(7) position of the phenothiazine. The introduction of a donor unit at the C(7) position exhibited a weak impact on the optical and electrochemical characteristics of the compounds and led to amorphous films with bulk hole mobilities in the typical range reported for phenothiazines, despite the higher charge delocalisation as attested by computational studies. In contrast, highly ordered films were formed when using the C(7)-unsubstituted 3-malononitrile phenothiazine, exhibiting an outstanding mobility of 1 × 10−3 cm2 V−1 s−1, the highest reported for this class of compounds. Computational conformational analysis of the new phenothizanes suggested that free rotation of the substitutents at the C(7) position suppresses the ordering of the system, thereby hampering suitable packing of the new materials needed for high charge carrier mobility.

show abstract

Section: Resultssupporting

confidence: 89%

Crystallisation-enhanced bulk hole mobility in phenothiazine-based organic semiconductors

Shinde

Salunke

Candeias

et al. 2017

Sci Rep

View full text Add to dashboard Cite

show abstract

“…However, ferric complexes of PL-derived hydrazones may have cytotoxic effects because of the induction of oxidative stress [17,18]. In general, hydrazones are versatile compounds gaining attention not only because of their biological activity, but also for their catalytic and fluorescent properties, which can be used for metal recognition and glass and phosphor production [19][20][21]. PLP-derived hydrazones have received less attention with regard to their biological activity than PL hydrazones.…”

Section: Introductionmentioning

confidence: 99%

Complexes of Gold(III) with Hydrazones Derived from Pyridoxal: Stability, Structure, and Nature of UV-Vis Spectra

Kuranova,

Pimenov,

Zavalishin

et al. 2024

IJMS

View full text Add to dashboard Cite

Pyridoxal and pyridoxal 5′-phosphate are aldehyde forms of B6 vitamin that can easily be transformed into each other in the living organism. The presence of a phosphate group, however, provides the related compounds (e.g., hydrazones) with better solubility in water. In addition, the phosphate group may sometimes act as a binding center for metal ions. In particular, a phosphate group can be a strong ligand for a gold(III) ion, which is of interest for researchers for the anti-tumor and antimicrobial potential of gold(III). This paper aims to answer whether the phosphate group is involved in the complex formation between gold(III) and hydrazones derived from pyridoxal 5′-phosphate. The answer is negative, since the comparison of the stability constants determined for the gold(III) complexes with pyridoxal- and pyridoxal 5′-phosphate-derived hydrazones showed a negligible difference. In addition, quantum chemical calculations confirmed that the preferential coordination of two series of phosphorylated and non-phosphorylated hydrazones to gold(III) ion is similar. The preferential protonation modes for the gold(III) complexes were also determined using experimental and calculated data.

show abstract

“…In addition, hydrazone derivatives have been reported to exhibit a broad range of biological and pharmacological activities . Moreover, the unique azomethine structure endowed with nucleophilic properties has propagated the design for new branches such as covalent bond organic frameworks, , supramolecular chemistry, − dynamic combinatorial chemistry (DCC), and opto and hole-transporting-electronic devices . Based on this knowledge, it is expected that the introduction of the hydrazone group alongside another versatile functional group such as phosphinoyl moiety onto an alkene would constitute compounds that not only are amenable to further synthetic manipulations but also may potentially be of relevance in the materials and medicinal fields.…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Radical Hydrazono-Phosphorylation of Alkenes

et al. 2022

View full text Add to dashboard Cite

An efficient copper-catalyzed radical hydrazono-phosphorylation of alkenes with hydrazine derivatives and diarylphosphine oxides is described. The reaction provides a general and convenient method toward the synthesis of diverse β-hydrazonophosphine oxides in satisfactory yields. Based on conducted mechanistic experiments, a mechanism involving Ag-catalyzed oxidative generation of phosphinoyl radicals and subsequent addition to alkenes followed by Cu-assisted hydrazonation is proposed. Moreover, the practicability of the reaction is successfully demonstrated by its successful application on a gram scale.

show abstract

Hole-transporting phenothiazine-based hydrazones with reactive vinylbenzyl groups

Cited by 8 publications

References 30 publications

Crystallisation-enhanced bulk hole mobility in phenothiazine-based organic semiconductors

Crystallisation-enhanced bulk hole mobility in phenothiazine-based organic semiconductors

Complexes of Gold(III) with Hydrazones Derived from Pyridoxal: Stability, Structure, and Nature of UV-Vis Spectra

Copper-Catalyzed Radical Hydrazono-Phosphorylation of Alkenes

Contact Info

Product

Resources

About