Synthesis and study of new rod-like mesogens containing 2-aminothiophene unit

Puterová, Zita; Romiszewski, Jerzy; Mieczkowski, Józef; Górecka, Ewa

doi:10.1016/j.tet.2012.07.075

Cited by 19 publications

(13 citation statements)

References 47 publications

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“…Meanwhile, a strong absorption band of ν(C=O) was assigned at around 1694 cm -1 that related to the resonance and mesomeric effect of phenyl ring. Additionally, the presence of ν(C-O) (ether) stretching vibration can be observed at 1157 cm -1 respectively, in which it is highly indicated the compound was indeed aldehyde derivative and are in close agreement with previously studied system [15], [16].…”

Section: Resultssupporting

confidence: 86%

Assessment on Heck-Immine Derivatives as Organic Semiconductor Materials

Rahamathullah

Lim

Khairul

2018

MST

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This paper reports the synthetic, characterization and theoretical evaluation of new class of hybrid Heck-immine system involving mixed moieties of vinylene (C=C) and azomethines (CH=N) which has been successfully integrated into an addition of organic semiconducting materials. The assessment of 4-[(hexyloxyphenyl)methylene]amino)-4'-chlorostilbene (HEXCS) based on Donor (D)-π-Acceptor (A) was evaluated as active semiconductor material candidates via several spectroscopic and analytical techniques. In turn, the investigation of its potential as dopant system in conductive film was successfully deposited on indium tin oxide (ITO) coated substrate via spin coating method. The relationship between electronic and optical properties, chemical modelling at molecular interactions and electrical performances of the designated system were evaluated. In addition, the quantum mechanical calculation proved that the value of energy separation of HEXCS between HOMO and LUMO exhibits 3.09 eV which was in good agreement with the experimental result of optical band gap 3.10 eV. The findings from the thermal and conductivity analysis revealed that the developed film HEXCS exhibited good stability at high temperature and electrical performance with an increasing conductivity up to 0.1531 Scm -1 under maximum light intensity of 100 Wm -2 . Therefore, this proposed type of molecular framework has given an ideal indication to act as semiconductor material candidates potentially use in any designated electronic application. AbstractPenilaian Turunan Heck-Immine sebagai Material Organik Semikonduktor. Penelitian ini melaporkan tentang kajian sintetik, karakterisasi dan evaluasi teoritis bagi kelas baru dari sistem hibrid Heck-imina yang melibatkan perpaduan unsur vinilen (C=C) dan azometina (CH=N) yang telah berhasil diintegrasikan sebagai bahan tambahan pada material semikonduktor organik. Penilaian 4-[(heksiloksifenil)metilena]amino)-4'-kloro-stilben (HEXCS) berdasarkan donor (D)-π-penerima (A) dievaluasi sebagai kandidat bahan semikonduktor aktif melalui beberapa teknik spektroskopi dan analitis. Selanjutnya, penelitian mengenai potensinya sebagai sistem dopan pada film konduktif, HEXCS berhasil diendapkan pada substrat yang dilapisi indium tin oksida (ITO) melalui metode spin coating. Hubungan antara sifat elektronik dan optik, pemodelan kimia pada interaksi molekuler dan kinerja elektrik dari sistem ini juga telah dievaluasi. Sebagai tambahan, perhitungan mekanikal kuantum membuktikan bahawa nilai pemisahan energi HEXCS di antara HOMO dan LUMO adalah 3.09 eV, dimana nilai tersebut mendekati nilai eksperimen dengan nilai 3.10 eV. Temuan dari analisis termal dan konduktivitas menunjukkan bahwa film HEXCS yang dikembangkan menunjukkan stabilitas yang baik pada suhu tinggi dan kinerja elektrik yang baik dengan peningkatan nilai konduktivitas 0.1531 Scm -1 menggunakan intensitas cahaya maksimum sebesar 100 Wm -2 . Oleh karena itu, kerangka molekul yang diusulkan ini ideal digunakan sebagai kandidat material semikonduktor yang b...

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Section: Resultssupporting

confidence: 86%

Assessment on Heck-Immine Derivatives as Organic Semiconductor Materials

Rahamathullah

Lim

Khairul

2018

MST

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“…From a mechanistic point of view, when a reaction rate is enhanced under aqueous conditions, the acceleration is attributed to either the repulsive forces arising from hydrophobicity of the reactants 30 or to activation of electron donating functional groups through H-bonding with water molecules. 31 To study the role of these effects in the present work, we next altered the composition of the aqueous medium to investigate the effect of different additives on the progress of the reaction (entries [9][10][11][12][13][14]. In these cases, an early work-up procedure was used (after 0.5 h) so that a better comparison of the results could be concluded.…”

Section: Resultsmentioning

confidence: 99%

A facile four-component Gewald reaction under organocatalyzed aqueous conditions

Abaee¹,

Cheraghi²

2013

Arkivoc

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In the presence of water and triethylamine, a four-component process involving ethyl cyanoacetate, an α-methylene carbonyl compound, a primary or a secondary amine, and elemental sulfur leads to efficient room-temperature formation of 2-amino-3-carboxamide derivatives of thiophene in short time periods. The products, which precipitate from the reaction mixtures, are easily obtained by simple filtration and recrystallization from ethyl acetate/hexanes.

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“…11 Stilbenes also belong to systems that show reversible photoinduced cis-trans isomerization, 12 exhibit strong blue fluorescence 13 and as promesogenic entities in host thiophene-containing structures can introduce mesomorphic properties. 14 The optical anisotropy of such LC systems allows the generation of polarized light in OLEDs and polarized fluorescence which are of interest for security labels. [14][15][16][17][18] Advantage of both, azobenzene and stilbene elements, is their acceptable synthetic accessibility requiring only straightforward purification steps.…”

Section: Introductionmentioning

confidence: 99%

“…14 The optical anisotropy of such LC systems allows the generation of polarized light in OLEDs and polarized fluorescence which are of interest for security labels. [14][15][16][17][18] Advantage of both, azobenzene and stilbene elements, is their acceptable synthetic accessibility requiring only straightforward purification steps. 19,20 Their insertion into thiophene-based materials can lead to formation of a variety of mesomorphic structures with possible application for new types of optoelectronic devices.…”

Section: Introductionmentioning

confidence: 99%

“…33 The availability of reagents and the mild reaction conditions all contribute to the versatility of this reaction, where by choosing suitable substrates the structure of the final thiophene-containing material is precisely predicted. 14,33 Experimental Synthesis of all presented compounds is described in the ESI † (Schemes S1 and S2). Gold NPs were synthesized according to the Brust method, using n-decanethiol to passivate the metal surface.…”

Section: Introductionmentioning

confidence: 99%

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