Development of Step‐Saving Alternative Synthetic Pathways for Functional π‐Conjugated Materials

Liu, Ching Yuan; Lin, Po Han; Lee, Kun‐Mu

doi:10.1002/tcr.202100101

Cited by 6 publications

(2 citation statements)

References 47 publications

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“…Functional organic materials are one of the most important and emerging area of research in state-of-the-art materials science ( Li and Yu, 2021 ; Liu et al, 2021 ). Construction of potential high-performance materials as well as their essential components is needed to be achieved according to modern requirements of sustainable and environmentally-focused society.…”

Section: Introductionmentioning

confidence: 99%

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

et al. 2022

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Nitrogen-rich energetic materials comprised of a combination of several heterocyclic subunits retain their leading position in the field of materials science. In this regard, a preparation of novel high-energy materials with balanced set of physicochemical properties is highly desired. Herein, we report the synthesis of a new series of energetic salts incorporating a (1,2,4-triazolyl) furoxan core and complete evaluation of their energetic properties. All target energetic materials were well characterized with IR and multinuclear NMR spectroscopy and elemental analysis, while compound 6 was further characterized by single-crystal X-ray diffraction study. Prepared nitrogen-rich salts have high thermal stability (up to 232°C), good experimental densities (up to 1.80 g cm−3) and high positive enthalpies of formation (344–1,095 kJ mol−1). As a result, synthesized energetic salts have good detonation performance (D = 7.0–8.4 km s−1; p = 22–32 GPa), while their sensitivities to impact and friction are quite low.

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Section: Introductionmentioning

confidence: 99%

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

et al. 2022

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“…A creation of novel functional organic materials remains one of the urgent goals in modern chemistry and materials science [1][2][3][4]. Such materials constitute a large variety of usually conjugated organic compounds with different chemical and physical properties.…”

Section: Introductionmentioning

confidence: 99%

An Alliance of Polynitrogen Heterocycles: Novel Energetic Tetrazinedioxide-Hydroxytetrazole-Based Materials

2022

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Energetic materials constitute one of the most important subtypes of functional materials used for various applications. A promising approach for the construction of novel thermally stable high-energy materials is based on an assembly of polynitrogen biheterocyclic scaffolds. Herein, we report on the design and synthesis of a new series of high-nitrogen energetic salts comprising the C-C linked 6-aminotetrazinedioxide and hydroxytetrazole frameworks. Synthesized materials were thoroughly characterized by IR and multinuclear NMR spectroscopy, elemental analysis, single-crystal X-ray diffraction and differential scanning calorimetry. As a result of a vast amount of the formed intra- and intermolecular hydrogen bonds, prepared ammonium and amino-1,2,4-triazolium salts are thermally stable and have good densities of 1.75–1.78 g·cm−3. All synthesized compounds show high detonation performance, reaching that of benchmark RDX. At the same time, as compared to RDX, investigated salts are less friction sensitive due to the formed net of hydrogen bonds. Overall, reported functional materials represent a novel perspective subclass of secondary explosives and unveil further opportunities for an assembly of biheterocyclic next-generation energetic materials.

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New Molecular Design, Step‐Saving Synthesis, and Applications of Indolocarbazole Core‐Based Oligo(hetero)arenes

Lin,

Chiu,

Cao

et al. 2023

Chemistry An Asian Journal

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In this work, we have successfully synthesized 15 new examples (LLA01‐06; LinLi01‐10) of small‐molecule hole‐transporting materials (HTM) using the less explored indolocarbazole (ICbz) as core moiety. Different from previously reported ICbz HTMs, LinLi01‐10 exhibit new molecular designs in which 3,4‐ethylenedioxythiophene (EDOT) units are inserted as crucial π‐spacers and fluorine atoms are introdcued into end‐group molecules. These substantially improve the materials solubility and device power conversion efficiencies (PCEs) while fabricated in perovskite solar cells (PSC). More importantly, LinLi01‐10 are generated by a sustainable synthetic approach involving the use of straightforward C−H/C−Br couplings as key transformations, thus avoiding additional synthetic transformations including halogenation and borylation reactions called substrate prefunctionalizations usually required in Suzuki reactions. Most HTM molecules can be purified simply by reprecipitations instead of conducting column chromatography. In contrast to LLA01‐06 without additional EDOT moieties, PSC devices using LinLi01‐10 as hole‐transport layers display promising PCEs of up to 17.5 %. Interestingly, PSC devices employing seven of the LinLi01‐10 as hole‐transport molecules, respectively, are all able to show an immediate >10 % PCE (t=0) without any device oxidation/aging process that is necessary for the commercial spiro‐OMeTAD based PSCs.

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Development of Step‐Saving Alternative Synthetic Pathways for Functional π‐Conjugated Materials

Cited by 6 publications

References 47 publications

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

An Alliance of Polynitrogen Heterocycles: Novel Energetic Tetrazinedioxide-Hydroxytetrazole-Based Materials

New Molecular Design, Step‐Saving Synthesis, and Applications of Indolocarbazole Core‐Based Oligo(hetero)arenes

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