5,5′-Bis-(alkylpyridinyl)-2,2′-bithiophenes: synthesis, liquid crystalline behaviour and charge transport

Getmanenko, Yulia A.; Kang, Shin-Woong; Shakya, Naresh; Pokhrel, Chandra Prasad; Bunge, Scott D.; Kumar, Satyendra; Ellman, Brett; Twieg, Robert J.

doi:10.1039/c3tc31522c

Cited by 10 publications

(6 citation statements)

References 37 publications

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“…Upon further cooling below the transition at 91 °C, the POM textures develop striations across the fan-shaped regions, and the schlieren patterns blur into a mosaic texture (Figure 3b). These changes are commonly associated with the formation of more highly ordered smectic phases [47,48,79,80], which is further supported by the XRD data (Figure 4b). The lamellar d 001 , d 002 and d 003 peaks become more pronounced, signifying an increase in long-range layer ordering, and the layer spacing increases to 33.3 Å, from 30.1 Å in the SmC phase.…”

Section: Resultssupporting

confidence: 69%

Heterocycle Effects on the Liquid Crystallinity of Terthiophene Analogues

et al. 2019

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Liquid crystalline self-assembly offers the potential to create highly ordered, uniformly aligned, and defect-free thin-film organic semiconductors. Analogues of one of the more promising classes of liquid crystal semiconductors, 5,5”-dialkyl-α-terthiophenes, were prepared in order to investigate the effects of replacing the central thiophene with either an oxadiazole or a thiadiazole ring. The phase behaviour was examined by differential scanning calorimetry, polarized optical microscopy, and variable temperature x-ray diffraction. While the oxadiazole derivative was not liquid crystalline, thiadiazole derivatives formed smectic C and soft crystal lamellar phases, and maintained lamellar order down to room temperature. Variation of the terminal alkyl chains also influenced the observed phase sequence. Single crystal structures revealed the face-to-face orientation of molecules within the layers in the solid-state, a packing motif that is rationalized based on the shape and dipole of the thiadiazole ring, as corroborated by density functional theory (DFT) calculations. The solution opto-electronic properties of the systems were characterized by absorption and emission spectroscopy, cyclic voltammetry, and time-dependent density functional theory (TD-DFT).

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Section: Resultssupporting

confidence: 69%

Heterocycle Effects on the Liquid Crystallinity of Terthiophene Analogues

et al. 2019

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“…7(a) and (d)). These textures are indicative of the formation of the higher ordered tilted phase, and although these textures are very similar to the textures of the crystal G phase that formed from the SmF phase, 44 certain assignment is not possible.…”

Section: Liquid Crystalline Behaviormentioning

confidence: 92%

“…S36 ‡). Since the incorporation of the pyridine ring into the aromatic core in some cases results in a complex LC behavior, 44 we also prepared the DTT derivatives 11a and 11b (Table 2) with 5alkylpyridin-2-yl rings instead of alkylthiophenes to potentially induce formation of the higher order phases.…”

Section: Liquid Crystalline Behaviormentioning

confidence: 99%

“…The benzene derivative has the most complex mesomorphic behavior in this series, with the transition to isotropic liquid at a relatively low temperature of 136.1 C, which might allow the lm formation by melting of the sample. While it is known that in some cases 44 substitution of benzene for pyridine results in a more complex LC behavior, for this particular architecture pyridine derivative 3f has a very simple mesomorphic behavior with the formation of only one LC phase.kk The isotropisation temperature of pyridine derivative 3f is lower in comparison with benzene derivative 2a (122.1 C vs. 136.1 C, respectively); for both materials the SmF phase was the rst phase that formed from the isotropic liquid, but in the case of pyridine derivative 3f the SmF phase exists for a much wider temperature range (45.3 C vs. 11.4 C). Change of the substitution pattern from 2,5-pyridine in 3f to 2,6-pyridine in 8a (ESI ‡) resulted in elimination of LC behaviour (no LC behaviour was observed for thiophene based mesogen tetra(5-pentadecylthiophen-2-yl)thiophene (9a)).…”

Section: Liquid Crystalline Behaviormentioning

confidence: 99%

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Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors

et al. 2014

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Mesogens with a general structure bis(alkylthiophene)arene, in which the central arene moiety is 1,4-benzene, 2,5-pyridine, 3,6-pyrimidine, 2,6-naphthalene and 2,6-dithieno[3,2-b;2 0 ,3 0 -d]thiophene, were synthesized, and the effect of the central unit and the length of the alkyl chains on the liquid crystalline behavior was studied by differential scanning calorimetry and polarized optical microscopy, and in the case of 1,4-bis(5-tridecylthiophen-2-yl)benzene (2a) and 2,6-bis(5-tridecylthiophen-2-yl)DTT by synchrotron X-ray analysis. Several 2,5-bis(5-alkylthiophen-2-yl)pyridines and 1,4-bis(5tridecylthiophen-2-yl)benzene 2a exhibit a rare transitionformation of the SmF phase directly from the isotropic liquid; in the case of 2a, formation of higher ordered smectic phases was observed on further cooling. Hole-transporting properties of 2a in different mesophases were studied by the time-of-flight technique. The hole mobility, m h , in SmF reached 6 Â 10 À3 cm 2 V À1 s À1 and increased with an increase of the order of the mesophase up to 0.02 cm 2 V À1 s À1 in the S1 phase (tentatively assigned as the crystal G phase), $0.09 cm 2 V À1 s À1 in the S2 phase (tentatively assigned as the crystal H phase), and 0.11 cm 2 V À1 s À1 in the crystalline phase at 70 C.

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“…Twieg and co-workers used both Negishi and Kumada-Tamao-Corriu couplings in the course of a synthesis of liquid-crystalline materials. 15 5,5′-Di(alkylpyridyl)-2,2′-bithiophenes, such as 2,2′-(2,2′-bithiene-5,5′-diyl)bis(5-heptylpyridine) (CITKUN), were obtained by deprotolithiation, transmetalation with zinc, palladium-catalyzed Negishi coupling, and subsequent nickel-catalyzed Kumada-Tamao-Corriu coupling to introduce the alkyl chains (Scheme 8).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Synthesis of Heterobiaryls Featuring 1,4 N···S Inter-Ring Interactions

2015

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International audienceBecause of its low-lying σ* orbitals, the C-S bond can interact with electron donors. In this short review, our goal is to focus on intramol. interactions between bivalent sulfur and basic nitrogen atoms. In particular, we will consider the synthesis of selected heterobiaryls for which 1,4 N···S inter-ring interactions can be identified from X-ray diffraction data. Finally, we will briefly touch on the use of such conformational preferences in various applications. 1 Introduction 2 Cross-Coupling with C-C Bond Formation 3 Cross-Coupling with C-N Bond Formation 4 Nucleophilic Addn. to Azine Followed by Oxidn. 5 Multicomponent Reactions 6 Heterobiaryl Formation by Azine Building 7 Heterobiaryl Formation by Building of the Sulfur-Contg. Heterocycle 8 Cycloaddn. Reactions 9 Other Syntheses 10 Conclusion

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5,5′-Bis-(alkylpyridinyl)-2,2′-bithiophenes: synthesis, liquid crystalline behaviour and charge transport

Cited by 10 publications

References 37 publications

Heterocycle Effects on the Liquid Crystallinity of Terthiophene Analogues

Heterocycle Effects on the Liquid Crystallinity of Terthiophene Analogues

Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors

Synthesis of Heterobiaryls Featuring 1,4 N···S Inter-Ring Interactions

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