Multi-substituted triazatruxene-functionalized pyrene derivatives as efficient organic laser gain media

Sang, Ming; Cao, Sizhen; Yi, Jianpeng; Huang, Wei; Lai, Wen‐Yong; Huang, Wei

doi:10.1039/c5ra25530a

Cited by 27 publications

(22 citation statements)

References 49 publications

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“…General procedure for the synthesis of compound 4: [18] To a cooled (À78 8C) solution of 3 (500 mg, 0.74 mmol) in THF (25 mL), nBuLi (0.51 mL, 0.81 mmol) was added dropwise and the mixture was stirred for 1h.T hen 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (165 mg, 0.89 mmol) was added to the mixture and stirred for another 1h.T he mixture was warmed to room temperature and the solvent was evaporated to dryness. The crude was dissolved in CH 2 Cl 2 and was washed with water (3 30 mL) and dried over anhydrous Na 2 SO 4 .A fter removal of the solvent under vacuum, the residue was purified by column chromatography (silica gel, CH 2 Cl 2 /PE, 50:50) to furnish pure 4 (350 mg, 66 %) as a colourless oil.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Bonding as a Supramolecular Tool for Robust OFET Devices

Mula

Han

Heiser

et al. 2019

Chemistry A European J

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In the present study, we demonstrated the effect of hydrogen bonding in the semiconducting behaviour of a small molecule used in organic field-effect transistors (OFETs). For this study,t he highly soluble dumbbell-shaped molecule, Boc-TATDPP based on aB oc-protected thiophenediketopyrrolopyrrole (DPP) and triazatruxene (TAT)m oieties was used. The two Boc groups of the molecule were removed by annealing at 200 8C, which createdas trong hydrogen-bonded network of NH-TATDPP supported by additional p-p stacking. These were characterised by thermogravimetric analysis (TGA), UV/Vis and IR spectroscopy,X RD and high-resolution (HR)-TEM measurements. FETsw ere fabricat-ed with the semiconducting channel made of Boc-TATDPP and NH-TATDPP separately.I ti sw orth mentioning that the Boc-TATDPP film can be cast from solutiona nd then annealedt og et the other systemsw ithN H-TATDPP.M ore importantly,NH-TATDPP showedsignificantly higherhole mobilities compared to Boc-TATDPP.I nterestingly,t he high hole mobility in the case of NH-TATDPP was unaffectedu pon blendingw ith [6,6]-phenyl-C71-butyrica cid methyl ester (PC 71 BM). Thus, this robust hydrogen-bonded supramolecular network is likely to be useful in designing efficient and stable organico ptoelectronic devices.[**] OFET = organicfield-effect transistor.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Section: Methodsmentioning

confidence: 99%

Hydrogen Bonding as a Supramolecular Tool for Robust OFET Devices

Mula

Han

Heiser

et al. 2019

Chemistry A European J

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“…Subsequently, we developed two new pyrene derivatives substituted with triazatruxene at 1, 6-and 1, 3, 6, 8-positions, namely Py-2TAT (16) and Py-4TAT (17). [41] The integration of pyrene and triazatruxene into a monodisperse multi-substituted structure endowed the resulting molecules with excellent thermal stabilities, easy solution processing, and improved optical and electrical characteristics. The PL spectra of Py-2TAT in the film were similar to those from the dilute solution, while Py-4TAT showed an emission peak at 514 nm, which were red-shifted about 21 nm compared with its solution spectra, implying weak intermolecular interactions in the condensed states.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Design and Synthesis of Conjugated Starburst Molecules for Optoelectronic Applications

Liu

Lai

et al. 2018

The Chemical Record

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In recent years, conjugated starburst molecules, which possess a core unit with radial arms linked to the central axle, have become the research topic owing to their well-defined chemical structures, good solution processability, excellent reproducibility, and superior optoelectronic properties. The increasing interest in starburst systems is evidenced by progressively more frequent investigation on the use of these materials in optoelectronics. The ability to modify chemical structures through control over the core and arms on a molecular level can directly affect the electronic and electroluminescent characteristics of the resulting materials. In this review, we summarize and discuss main progress in our group concerning the rapidly developing field, in which strategies for the design and construction of starbursts are presented at length. Moreover, their application in organic light-emitting diodes (OLEDs) and organic semiconductor lasers (OSLs) are demonstrated as well, exploring the influence of molecular structures on the optoelectronic properties. Challenges and outlooks are also given at last.

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“…Sang et al . have synthesized a set of pyrene derivatives containing triazatruxene at the 1,6‐ and 1,3,6,8‐positions. They were Py‐2TAT ( 80 ) and Py‐4TAT ( 81 ) (Scheme ).…”

Section: The Triazatruxene Scaffoldmentioning

confidence: 99%

Synthetic Routes to Electroactive Organic Discotic Aromatic Triazatruxenes

Sayed

2017

Journal of Heterocyclic Chem

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This paper gives a survey about the triazatruxene (triindole) particle, distinguishes its structure, and portrays a conceivable way to deal with its combination and structures of all at-present-known fluid precious stones in view of triazatruxene, in addition to checking its electronic element criticalness. Triazatruxene is a brilliant particle that has been uncovered in the recent 14 years as a discotic liquid crystal compound. Of late, this electron-rich particle turned out to be more alluring as a core center in the building of discotic liquid column with electro-dynamic properties that demonstrated a consistent hexagonal columnar mesophase under an expansive assortment of temperatures. Besides, numerous different properties in this delicate material brought a wide consideration up in organic electronic innovation devices, for example, light radiating diodes (organic light-emitting diode), field impact transistors (field-effect transistor), and photovoltaic cells. In this survey, triazatruxene and all particles closely resembling triazatruxene in the most recent 16 years until 2016 have been incorporated, including a brief summary of their applications in all fields, which will be introduced.

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Multi-substituted triazatruxene-functionalized pyrene derivatives as efficient organic laser gain media

Abstract: A set of pyrene derivatives substituted with multiple triazatruxenes were synthesized and explored as efficient gain media for organic lasers.

Cited by 27 publications

References 49 publications

Hydrogen Bonding as a Supramolecular Tool for Robust OFET Devices

Hydrogen Bonding as a Supramolecular Tool for Robust OFET Devices

Design and Synthesis of Conjugated Starburst Molecules for Optoelectronic Applications

Synthetic Routes to Electroactive Organic Discotic Aromatic Triazatruxenes

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