Synthesis and Structure of Boron–Bithiazole Complexes

Findlater, Michael; Swisher, Nicholas S.; White, Peter S.

doi:10.1002/ejic.201000940

Cited by 6 publications

(4 citation statements)

References 20 publications

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“…As all of the devices in this study were fabricated simultaneously under the same conditions, we speculate that hole traps specific to PDBPyBTz are the source of the unipolar charge transport. Bithiazole has been reported to form complexes with Lewis acids, and we speculate that such interactions may be occurring with the BTz moieties in PDBPyBTz and the hole charge carriers, effectively blocking hole transport.…”

Section: Resultsmentioning

confidence: 88%

Synergistic Use of Bithiazole and Pyridinyl Substitution for Effective Electron Transport Polymer Materials

et al. 2019

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The development of semiconducting conjugated polymers for organic field effect transistors (OFETs) has been the focus of intense research efforts for their key role in plastic electronics as well as a vision of solution processability leading to reduced costs in device fabrication relative to those of their inorganic counterparts. The pursuit of high-performance n-channel (electron-transporting) polymer semiconductors vital to the development of robust and low-cost organic integrated circuits has faced significant challenges, mainly for poor ambient operational stability and OFET device performance lagging far behind that of pchannel organic semiconductors. As an alternative to the ubiquitous donor−acceptor molecular design strategy, an all-acceptor (A−A) unipolar approach was implemented in the design of poly(2-(2decyltetradecyl)-6-(5-(5′-methyl[2,2′-bithiaol]-5-yl)-3-(5-methylpyridin-2-yl)-5-(tricosan-11-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (PDBPyBTz). The n-channel copolymer allowed investigation of the impact of electron-withdrawing moieties on conjugated polymer device performance and the utility of the A−A molecular design strategy. As an analogue to benzene, the pyridines flanking the diketopyrrolopyrrole moiety in PDBPyBTz were strategically chosen to lower the energy levels and impart planarity to the monomer, both of which aid in achieving stable n-channel performance. Incorporation of PDBPyBTz into a bottom-gate/bottom-contact OFET afforded a device that exhibited unipolar electron transport. In addition to developing a high-performance n-channel polymer, this study allowed for an investigation of structure−property relationships crucial to the design of such materials in high demand for sustainable technologies, including organic photovoltaics and other solution-processed organic electronic devices.

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Section: Resultsmentioning

confidence: 88%

Synergistic Use of Bithiazole and Pyridinyl Substitution for Effective Electron Transport Polymer Materials

et al. 2019

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“…The target, 5,5 ′ -bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4 ′ -diphenyl-2,2 ′ -bithiazole (6), was synthesized via our adapted Stille coupling protocol developed for halothiadiazines [12]. The starting material, bithiazole 7, was readily obtained in two steps with an overall yield of 58%, starting from 2-bromoacetophenone and rubeanic acid [11,18]. Additionally, the tributylstannyl reagent, 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole (8), had been previously used effectively by us to prepare thiadiazine oligomers [12].…”

Section: Resultsmentioning

confidence: 99%

5,5′-Bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole

Kalogirou,

Koutentis

2024

Molbank

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“…Having established the ability of PNDI2Tz to interact with strong protic acids, the investigation was extended to explore the impact of exposure to neutral Lewis acid species. Specifically, BF 3 was selected as a representative example given its ready availability, commercial significance, known environmental health and safety issues, and relatively low LC 50 . − As stated in the AEGL book, the AEGL-3 can be treated as the LC 50 for BF 3 , which is at 436.22 ppm (1210 mg/m 3 ) for rats on 4 h exposure . In this study, fresh anhydrous BF 3 ·OEt 2 was used as the source of BF 3 to facilitate handling.…”

Section: Resultsmentioning

confidence: 99%

More Than Another Halochromic Polymer: Thiazole-Based Conjugated Polymer Transistors for Acid-Sensing Applications

Yuan

Hamrock

et al. 2020

ACS Appl. Polym. Mater.

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Stimuli-responsive π-conjugated materials present opportunities for chemical sensing, whereby through interaction with an analyte the π-conjugated system undergoes a change in molecular geometry and/or electronic structure which can be detected as a change in either the optical or electrical characteristics. Here, a naphthalene diimide donor–acceptor conjugated polymer, poly(2,7-bis(2-decyltetradecyl)-4-methyl-9-(5′-methyl-[2,2′-bithiazol]-5-yl)benzo[lmn][3,8]-phenanthroline-1,3,6,8(2H,7H)-tetraone) (PNDI2Tz), is reported as an acid sensing material. Shifts in the UV–vis spectroscopic signature of PNDI2Tz in the presence of protic and Lewis acids were investigated. In addition, PNDI2Tz-based n-channel organic field-effect transistors (OFETs) were fabricated and shown to respond to the gas phase Lewis acid, boron trifluoride (BF3), whereby the transistors reproducibly turn off in the presence of 60 ppm BF3.

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Synthesis and Structure of Boron–Bithiazole Complexes

Cited by 6 publications

References 20 publications

Synergistic Use of Bithiazole and Pyridinyl Substitution for Effective Electron Transport Polymer Materials

Synergistic Use of Bithiazole and Pyridinyl Substitution for Effective Electron Transport Polymer Materials

5,5′-Bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole

More Than Another Halochromic Polymer: Thiazole-Based Conjugated Polymer Transistors for Acid-Sensing Applications

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