Base-Catalyzed H/D Exchange Reaction of Difluoromethylarenes

Huang, Liang; Liu, Wei; Zhao, Liu−Bin; Zhang, Zengyu; Yan, Xiaoyu

doi:10.1021/acs.joc.0c02827

Cited by 33 publications

(26 citation statements)

References 58 publications

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“…Furthermore, we found the relative deuterated yield for other pyridine derivatives, N , N ‐dimethylpyridin‐4‐amine, 4‐( tert ‐butyl)pyridine, 2‐(4‐(trifluoromethyl)phenyl)pyridine, 2,2′‐bipyridine, 4‐chloro‐7‐(trifluoromethyl)quinoline, quinoline and phenanthroline, can also be consistent with an anionic mechanism (Figure S11.1–S11.7). Besides, excellent correlation between relative thermal stability of anionic species and deuteration yield are also found for other experimental results [25,28b] of the remote deuteration of pyridine derivatives, such as pyridine, 3,4‐dimethylpyridine, 2,3‐dimethylpyridine, 2‐bromopyridine, 2‐bromo‐5‐methylpyridine, 6‐bromonicotinonitrile and 1‐(difluoromethyl)‐4‐fluorobenzene (Figure S11.8–S11.14), as well as the deuteration of bioactive molecules in our own scope (caffeine, Figure S11.15). Using the anion stabilities, we have been able to successfully predict the order of deuterium incorporation in the different positions of new substrates (Scheme 6, Figure S11.16–S11.19).…”

Section: Resultssupporting

confidence: 83%

“…Further, some bioactive molecules could be successfully labeled applying our methodology (Scheme 3, compounds 29 – 37 ). For these molecules, deuterium was not only incorporated in heterocycles (Scheme 3, compounds 29‐ d , 30‐ d , 33‐ d 3 , 34‐ d 3 , 36‐ d 3 , 37‐ d ) but also in chloro‐substituted arenes (Scheme 3, 32‐ d , 34‐ d 11 , 35‐ d 4 ) as previously reported for HIE reactions using KO t Bu and DMSO‐ d 6 [28b] …”

Section: Resultsmentioning

confidence: 91%

“…In general, the combination of DMSO and KO t Bu is considered as a super‐base system [37] and the corresponding anionic mechanism has been proposed [28b] . Thus, we calculated the relative Gibbs free energies of the anionic species of 2‐phenylpyridine (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

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Base‐Mediated Remote Deuteration of N‐Heteroarenes – Broad Scope and Mechanism

et al. 2022

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Deuterated organic molecules provide the basis for many applications in life sciences and material research. Thus, methodologies to access labeled compounds with defined selectivity continue to be important. Using KOtBu as base and DMSO‐d6 as deuterium source, we present a general and applicable method for the selective deuteration of a set of nitrogen‐containing heterocycles (pyridines, azines and bioactive molecules). Experimental and DFT mechanistic studies indicate that this reaction proceeds via deprotonation of the substrates by the dimsyl anion. The relative thermodynamic stability of the heterocycle anions determines the distribution and degree of deuteration.

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Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 91%

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Base‐Mediated Remote Deuteration of N‐Heteroarenes – Broad Scope and Mechanism

et al. 2022

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“…The maximum mobility of devices is ≈1.2 cm 2 V −1 s −1 . [ 127 ] In order to produce high‐quality thin film, researchers usually combine the thermal evaporation with other techniques. Zone‐casting was first used to form C8‐BTBT parallel ribbons and then supplementary C8‐BTBT was deposited by thermal evaporation in high‐vacuum environment ( Figure a).…”

Section: Fabrication Techniques Of Btbt Derivative Thin Filmmentioning

confidence: 99%

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Xie

Liu

Sun

et al. 2022

Adv Funct Materials

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1]benzothieno[3,2-b]benzothiophene (BTBT), with two benzene rings as the outermost rings, is referred to as diacene-fused ladder-type π-conjugated thienothiophenes. During the last three decades, derivatives based on BTBT core have been extensively studied due to their tremendous application prospects in organic field-effect transistors (OFETs) and organic optoelectronic devices. In order to further advance the development of organic electronics, new materials are constantly being synthesized and new methods are constantly evolving. This review mainly focuses on the crystal and electronic structures of BTBT derivatives, the soluble and thermal properties, the fabrication methods, as well as the strategies for performance improvement and optoelectronic applications including OFETs, photodetectors, synaptic devices, and organic light-emitting transistors. As one of the most promising organic materials, the insight into BTBT-based molecules will accelerate their potential application and provide important reference value for the development toward commercialized and industrialized organic semiconducting products.

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“…In these two devices, a representative organic semiconductor of C 8 ‐BTBT was selected as the conducting layer because of its superior carrier mobility and good film‐forming character. [ 50–53 ] As for CTB layer, here another organic semiconductor of TAPC was used with the consideration of its appropriate mobility contrast with that of C 8 ‐BTBT, the matched energy level, as well as its wide use as the hole transporting layer in emitting devices. [ 19,54,55 ] Chemical structures of all materials used in this research are together shown in Scheme S1 in the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

Redistributed Current Density in Lateral Organic Light‐Emitting Transistors Enabling Uniform Area Emission with Good Stability and Arbitrary Tunability

et al. 2022

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Organic light‐emitting transistors (OLETs), integrating the functions of an organic field‐effect transistor (OFET) and organic light‐emitting diode (OLED) in a single device, are promising for the next‐generation display technology. However, the great challenge of achieving uniform area emission in OLETs with good stability and arbitrary tunability hinders their development in this field. Herein, an effective solution to obtain well‐defined area emission in lateral OLETs by incorporating a charge‐transport buffer (CTB) layer between the conducting channel and emitting layer is proposed. Comprehensive theoretical simulation and experimental results demonstrate redistributed potential beneath the drain electrode under the shielding effect of the CBT layer, resulting in a highly uniform current density. In this case, uniform recombination of balanced holes and electrons can be guaranteed, which is essential for the formation of area emission in the following OLETs. RGB OLETs with uniform area emission are constructed, which show good gate tunable ability (ON/OFF ratio 106), high loop stability (over 200 cycles) and high aperture ratio (over 80%) due to the arbitrary tunability of the device geometry. This work provides a new avenue for constructing area‐emission lateral OLETs, which have great potential for display technology because of their good compatibility with conventional fabrication techniques.

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Base-Catalyzed H/D Exchange Reaction of Difluoromethylarenes

Cited by 33 publications

References 58 publications

Base‐Mediated Remote Deuteration of N‐Heteroarenes – Broad Scope and Mechanism

Base‐Mediated Remote Deuteration of N‐Heteroarenes – Broad Scope and Mechanism

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Redistributed Current Density in Lateral Organic Light‐Emitting Transistors Enabling Uniform Area Emission with Good Stability and Arbitrary Tunability

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