Calix[4]resorcinarene macrocycles: Synthesis, thermal behavior and crystalline characterization

Larbi Eddaif, László Trif, J. Telegdi, O. Egyed, A. Shaban

???family-name???: Article

Abstract

Supramolecular chemistry is an interdisciplinary scientific field, including chemical, physical and biological properties of more complex chemical species than the molecules themselves. Calixarenes/calixresorcinarenes are macrocyclic compounds, consisting of ‘n’ phenolic/resorcinolic units linked together by methylene bridges; these macrocycles are often used for molecular recognition. Thus, different modifications can be made to both the lower and upper rim, allowing the construction of well-defined multivalent buildings. In this work, three calix[4]resorcinarene macrocycles were synthesized, namely C-dec-9-en-1-ylcalix[4]resorcinarene (CAL 11U), C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene (CAL 9U) and C-nonylcalix[4]resorcinarene (CAL 10) by a simple condensation reaction. The compounds CAL 11U and CAL 10 have been already synthesized by researchers, while the CAL 9U has been synthesized for the first time. Their structures were confirmed using ATR-FTIR, 1H NMR and 13C NMR. Thermal analysis combined with mass spectrometric evolved analysis of the vapors was used to study the thermal behavior of the different synthesized molecules, and they were the subject of characterization by X-ray powder diffraction in order to analyze their degree of crystallinity.

???language???English
???journalAssociation???Journal of Thermal Analysis and Calorimetry
???DOIs???
???publicationStatus???Accepted/In press - jan. 1 2019

Fingerprint

Supramolecular chemistry
Condensation reactions
X ray powder diffraction
Thermoanalysis
Mass spectrometry
thermal analysis
mass spectroscopy
Nuclear magnetic resonance
Crystalline materials
Hungary
Molecular recognition
nuclear magnetic resonance
Molecules
synthesis
rims
methylene
molecules
crystallinity
Macrocyclic Compounds
condensation

Keywords

    ASJC Scopus subject areas

    • Condensed Matter Physics
    • Physical and Theoretical Chemistry

    Cite this

    @article{3733ef54f271429787a7dd9a6aeb3a94,
    title = "Calix[4]resorcinarene macrocycles: Synthesis, thermal behavior and crystalline characterization",
    abstract = "Supramolecular chemistry is an interdisciplinary scientific field, including chemical, physical and biological properties of more complex chemical species than the molecules themselves. Calixarenes/calixresorcinarenes are macrocyclic compounds, consisting of ‘n’ phenolic/resorcinolic units linked together by methylene bridges; these macrocycles are often used for molecular recognition. Thus, different modifications can be made to both the lower and upper rim, allowing the construction of well-defined multivalent buildings. In this work, three calix[4]resorcinarene macrocycles were synthesized, namely C-dec-9-en-1-ylcalix[4]resorcinarene (CAL 11U), C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene (CAL 9U) and C-nonylcalix[4]resorcinarene (CAL 10) by a simple condensation reaction. The compounds CAL 11U and CAL 10 have been already synthesized by researchers, while the CAL 9U has been synthesized for the first time. Their structures were confirmed using ATR-FTIR, 1H NMR and 13C NMR. Thermal analysis combined with mass spectrometric evolved analysis of the vapors was used to study the thermal behavior of the different synthesized molecules, and they were the subject of characterization by X-ray powder diffraction in order to analyze their degree of crystallinity.",
    keywords = "Calixresorcinarenes, FTIR, Synthesis, Thermal analysis, XRD",
    author = "Larbi Eddaif and L{\'a}szl{\'o} Trif and J. Telegdi and O. Egyed and A. Shaban",
    year = "2019",
    month = "1",
    day = "1",
    doi = "10.1007/s10973-018-7978-0",
    language = "English",
    journal = "Journal of Thermal Analysis and Calorimetry",
    issn = "1388-6150",
    publisher = "Springer Netherlands",

    }

    TY - JOUR

    T1 - Calix[4]resorcinarene macrocycles

    T2 - Journal of Thermal Analysis and Calorimetry

    AU - Eddaif, Larbi

    AU - Trif, László

    AU - Telegdi, J.

    AU - Egyed, O.

    AU - Shaban, A.

    PY - 2019/1/1

    Y1 - 2019/1/1

    N2 - Supramolecular chemistry is an interdisciplinary scientific field, including chemical, physical and biological properties of more complex chemical species than the molecules themselves. Calixarenes/calixresorcinarenes are macrocyclic compounds, consisting of ‘n’ phenolic/resorcinolic units linked together by methylene bridges; these macrocycles are often used for molecular recognition. Thus, different modifications can be made to both the lower and upper rim, allowing the construction of well-defined multivalent buildings. In this work, three calix[4]resorcinarene macrocycles were synthesized, namely C-dec-9-en-1-ylcalix[4]resorcinarene (CAL 11U), C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene (CAL 9U) and C-nonylcalix[4]resorcinarene (CAL 10) by a simple condensation reaction. The compounds CAL 11U and CAL 10 have been already synthesized by researchers, while the CAL 9U has been synthesized for the first time. Their structures were confirmed using ATR-FTIR, 1H NMR and 13C NMR. Thermal analysis combined with mass spectrometric evolved analysis of the vapors was used to study the thermal behavior of the different synthesized molecules, and they were the subject of characterization by X-ray powder diffraction in order to analyze their degree of crystallinity.

    AB - Supramolecular chemistry is an interdisciplinary scientific field, including chemical, physical and biological properties of more complex chemical species than the molecules themselves. Calixarenes/calixresorcinarenes are macrocyclic compounds, consisting of ‘n’ phenolic/resorcinolic units linked together by methylene bridges; these macrocycles are often used for molecular recognition. Thus, different modifications can be made to both the lower and upper rim, allowing the construction of well-defined multivalent buildings. In this work, three calix[4]resorcinarene macrocycles were synthesized, namely C-dec-9-en-1-ylcalix[4]resorcinarene (CAL 11U), C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene (CAL 9U) and C-nonylcalix[4]resorcinarene (CAL 10) by a simple condensation reaction. The compounds CAL 11U and CAL 10 have been already synthesized by researchers, while the CAL 9U has been synthesized for the first time. Their structures were confirmed using ATR-FTIR, 1H NMR and 13C NMR. Thermal analysis combined with mass spectrometric evolved analysis of the vapors was used to study the thermal behavior of the different synthesized molecules, and they were the subject of characterization by X-ray powder diffraction in order to analyze their degree of crystallinity.

    KW - Calixresorcinarenes

    KW - FTIR

    KW - Synthesis

    KW - Thermal analysis

    KW - XRD

    UR - http://www.scopus.com/inward/record.url?scp=85059572164&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=85059572164&partnerID=8YFLogxK

    U2 - 10.1007/s10973-018-7978-0

    DO - 10.1007/s10973-018-7978-0

    M3 - Article

    JO - Journal of Thermal Analysis and Calorimetry

    JF - Journal of Thermal Analysis and Calorimetry

    SN - 1388-6150

    ER -