Donor Substituted Pyrazabole Monomers and Dimers: Design, Synthesis and Properties

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  • Indian Institute of Technology Indore (IITI)
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OriginalspracheEnglisch
Seiten (von - bis)415-420
Seitenumfang6
FachzeitschriftChemistrySelect
Jahrgang2
Ausgabenummer1
PublikationsstatusVeröffentlicht - 11 Jan. 2017

Abstract

We report the design and synthesis of ferrocene and triphenylamine substituted D–π– A–π–D and D–π–A–π–A–π–D type of symmetrical pyrazabole monomers (3 and 5) and dimers (6 and 7). Their optical, thermal, electrochemical and computational properties were investigated. The electronic absorption spectra of pyrazaboles 3−7 exhibit absorption bands in UV region. The TGA study reveals that pyrazaboles 3−7 show good thermal stability and pyrazabole monomers are thermally more stable as compared to pyrazabole dimers. The electrochemical studies show that pyrazaboles 3−7 exhibits one reversible oxidation and two reduction waves. The theoretical investigation shows that the triphenylamine substituted pyrazaboles (5 and 7) exhibit low HOMO − LUMO gap values compared to ferrocenyl pyrazaboles (3 and 6).

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Donor Substituted Pyrazabole Monomers and Dimers: Design, Synthesis and Properties. / Patil, Yuvraj; Jadhav, Thaksen; Dhokale, Bhausaheb et al.
in: ChemistrySelect, Jahrgang 2, Nr. 1, 11.01.2017, S. 415-420.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Patil Y, Jadhav T, Dhokale B, Butenschön H, Misra R. Donor Substituted Pyrazabole Monomers and Dimers: Design, Synthesis and Properties. ChemistrySelect. 2017 Jan 11;2(1):415-420. doi: 10.1002/slct.201601704
Patil, Yuvraj ; Jadhav, Thaksen ; Dhokale, Bhausaheb et al. / Donor Substituted Pyrazabole Monomers and Dimers : Design, Synthesis and Properties. in: ChemistrySelect. 2017 ; Jahrgang 2, Nr. 1. S. 415-420.
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abstract = "We report the design and synthesis of ferrocene and triphenylamine substituted D–π– A–π–D and D–π–A–π–A–π–D type of symmetrical pyrazabole monomers (3 and 5) and dimers (6 and 7). Their optical, thermal, electrochemical and computational properties were investigated. The electronic absorption spectra of pyrazaboles 3−7 exhibit absorption bands in UV region. The TGA study reveals that pyrazaboles 3−7 show good thermal stability and pyrazabole monomers are thermally more stable as compared to pyrazabole dimers. The electrochemical studies show that pyrazaboles 3−7 exhibits one reversible oxidation and two reduction waves. The theoretical investigation shows that the triphenylamine substituted pyrazaboles (5 and 7) exhibit low HOMO − LUMO gap values compared to ferrocenyl pyrazaboles (3 and 6).",
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author = "Yuvraj Patil and Thaksen Jadhav and Bhausaheb Dhokale and Holger Butensch{\"o}n and Rajneesh Misra",
note = "Funding information: Y. P. thanks Ministry of Human Resource Development (MHRD), T. J. and B. D. thank CSIR and University Grants Commission (UGC), New Delhi for their fellowships. R. M. thanks the Department of Science and Technology (Project No. EMR/2014/ 001257), New Delhi and Council of Scientific and Industrial Research (Project No. 01/(2795)/14/EMR-II), New Delhi for the financial support. We thank the Deutsche Forschungsgemein-schaft (Grant BU 814/26-1) Germany and INSA New Delhi. We also thank the Sophisticated Instrumentation Centre (SIC), Indian Institute of Technology (IIT) Indore.",
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T1 - Donor Substituted Pyrazabole Monomers and Dimers

T2 - Design, Synthesis and Properties

AU - Patil, Yuvraj

AU - Jadhav, Thaksen

AU - Dhokale, Bhausaheb

AU - Butenschön, Holger

AU - Misra, Rajneesh

N1 - Funding information: Y. P. thanks Ministry of Human Resource Development (MHRD), T. J. and B. D. thank CSIR and University Grants Commission (UGC), New Delhi for their fellowships. R. M. thanks the Department of Science and Technology (Project No. EMR/2014/ 001257), New Delhi and Council of Scientific and Industrial Research (Project No. 01/(2795)/14/EMR-II), New Delhi for the financial support. We thank the Deutsche Forschungsgemein-schaft (Grant BU 814/26-1) Germany and INSA New Delhi. We also thank the Sophisticated Instrumentation Centre (SIC), Indian Institute of Technology (IIT) Indore.

PY - 2017/1/11

Y1 - 2017/1/11

N2 - We report the design and synthesis of ferrocene and triphenylamine substituted D–π– A–π–D and D–π–A–π–A–π–D type of symmetrical pyrazabole monomers (3 and 5) and dimers (6 and 7). Their optical, thermal, electrochemical and computational properties were investigated. The electronic absorption spectra of pyrazaboles 3−7 exhibit absorption bands in UV region. The TGA study reveals that pyrazaboles 3−7 show good thermal stability and pyrazabole monomers are thermally more stable as compared to pyrazabole dimers. The electrochemical studies show that pyrazaboles 3−7 exhibits one reversible oxidation and two reduction waves. The theoretical investigation shows that the triphenylamine substituted pyrazaboles (5 and 7) exhibit low HOMO − LUMO gap values compared to ferrocenyl pyrazaboles (3 and 6).

AB - We report the design and synthesis of ferrocene and triphenylamine substituted D–π– A–π–D and D–π–A–π–A–π–D type of symmetrical pyrazabole monomers (3 and 5) and dimers (6 and 7). Their optical, thermal, electrochemical and computational properties were investigated. The electronic absorption spectra of pyrazaboles 3−7 exhibit absorption bands in UV region. The TGA study reveals that pyrazaboles 3−7 show good thermal stability and pyrazabole monomers are thermally more stable as compared to pyrazabole dimers. The electrochemical studies show that pyrazaboles 3−7 exhibits one reversible oxidation and two reduction waves. The theoretical investigation shows that the triphenylamine substituted pyrazaboles (5 and 7) exhibit low HOMO − LUMO gap values compared to ferrocenyl pyrazaboles (3 and 6).

KW - Cross-coupling

KW - Cyclic Voltammetry

KW - Density Functional Theory

KW - UV/Vis Spectroscopy.

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