Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

Ahmet Çetinkaya; Ali Enis Sadak; Mehmet Menaf Ayhan; Yunus Zorlu; Muhammet U. Kahveci

doi:10.1016/j.eurpolymj.2021.110664

Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

Ahmet Çetinkaya, Ali Enis Sadak, Mehmet Menaf Ayhan, Yunus Zorlu^*, Muhammet U. Kahveci

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Inverse electron demand Diels-Alder (IEDDA) reaction has been employed as a powerful ligation in several fields. In the current work, a synthetic approach relying on IEDDA reaction is developed for preparation of a porphyrin based covalent organic polymer (PoTz-COP). A tetra-norbornene functional porphyrin is chosen as the core and a bis-tetrazine as the linker. The PoTz-COP is readily formed by just mixing the components without a catalyst and under mild conditions. Chemical structure, morphology (XRD, SEM-EDX), porosity (BET), thermal stability (TGA), optical and gas sorption (CO₂ uptake) and selectivity (CO₂/N₂) properties via Myers and Prausnitz's ideal adsorbed solution theory (IAST) are investigated. PoTz-COP shows remarkably high adsorption selectivity of CO₂ over N₂ as found 80, 42, and 47 at 50/50 ratio; 84, 39 and 40 at 15/85 ratio; and 84, 39 and 38 at 05/95 ratio at temperatures of 273 K, 298 K and 320 K at 1.1 bar pressure respectively. The optical band gap is determined relatively narrow as 1.66 eV.

Original language	English
Article number	110664
Journal	European Polymer Journal
Volume	157
DOIs	https://doi.org/10.1016/j.eurpolymj.2021.110664
Publication status	Published - 15 Aug 2021

Bibliographical note

Publisher Copyright:
© 2021 Elsevier Ltd

Funding

M.U.K. thanks Turkish Academy of Sciences for financial support under Outstanding Young Scientists Award Program (TUBA-GEBIP). Y. Z. acknowledges support from The Science Academy, Young Scientist Award (BAGEP). A.C. is grateful to Council of Higher Education of Turkey (YOK 100/2000 PhD Scholarship) and to The Scientific and Technological Research Council of Turkey (2214-A, 1059B141700728) for financial support.

Funders	Funder number
Council of Higher Education of Turkey
TUBA-GEBIP
The Science Academy
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu	1059B141700728, 2214-A
Türkiye Bilimler Akademisi

Keywords

Covalent organic polymer
Gas sorption
Inverse electron demand Diels-Alder reaction
Selectivity
Tetrazine

Access to Document

10.1016/j.eurpolymj.2021.110664

Cite this

@article{86106c908e3144b792cb5fdc3fe909e8,

title = "Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction",

abstract = "Inverse electron demand Diels-Alder (IEDDA) reaction has been employed as a powerful ligation in several fields. In the current work, a synthetic approach relying on IEDDA reaction is developed for preparation of a porphyrin based covalent organic polymer (PoTz-COP). A tetra-norbornene functional porphyrin is chosen as the core and a bis-tetrazine as the linker. The PoTz-COP is readily formed by just mixing the components without a catalyst and under mild conditions. Chemical structure, morphology (XRD, SEM-EDX), porosity (BET), thermal stability (TGA), optical and gas sorption (CO2 uptake) and selectivity (CO2/N2) properties via Myers and Prausnitz's ideal adsorbed solution theory (IAST) are investigated. PoTz-COP shows remarkably high adsorption selectivity of CO2 over N2 as found 80, 42, and 47 at 50/50 ratio; 84, 39 and 40 at 15/85 ratio; and 84, 39 and 38 at 05/95 ratio at temperatures of 273 K, 298 K and 320 K at 1.1 bar pressure respectively. The optical band gap is determined relatively narrow as 1.66 eV.",

keywords = "Covalent organic polymer, Gas sorption, Inverse electron demand Diels-Alder reaction, Selectivity, Tetrazine",

author = "Ahmet {\c C}etinkaya and Sadak, {Ali Enis} and Ayhan, {Mehmet Menaf} and Yunus Zorlu and Kahveci, {Muhammet U.}",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = aug,

day = "15",

doi = "10.1016/j.eurpolymj.2021.110664",

language = "English",

volume = "157",

journal = "European Polymer Journal",

issn = "0014-3057",

publisher = "Elsevier Ltd",

}

TY - JOUR

T1 - Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

AU - Çetinkaya, Ahmet

AU - Sadak, Ali Enis

AU - Ayhan, Mehmet Menaf

AU - Zorlu, Yunus

AU - Kahveci, Muhammet U.

PY - 2021/8/15

Y1 - 2021/8/15

N2 - Inverse electron demand Diels-Alder (IEDDA) reaction has been employed as a powerful ligation in several fields. In the current work, a synthetic approach relying on IEDDA reaction is developed for preparation of a porphyrin based covalent organic polymer (PoTz-COP). A tetra-norbornene functional porphyrin is chosen as the core and a bis-tetrazine as the linker. The PoTz-COP is readily formed by just mixing the components without a catalyst and under mild conditions. Chemical structure, morphology (XRD, SEM-EDX), porosity (BET), thermal stability (TGA), optical and gas sorption (CO2 uptake) and selectivity (CO2/N2) properties via Myers and Prausnitz's ideal adsorbed solution theory (IAST) are investigated. PoTz-COP shows remarkably high adsorption selectivity of CO2 over N2 as found 80, 42, and 47 at 50/50 ratio; 84, 39 and 40 at 15/85 ratio; and 84, 39 and 38 at 05/95 ratio at temperatures of 273 K, 298 K and 320 K at 1.1 bar pressure respectively. The optical band gap is determined relatively narrow as 1.66 eV.

AB - Inverse electron demand Diels-Alder (IEDDA) reaction has been employed as a powerful ligation in several fields. In the current work, a synthetic approach relying on IEDDA reaction is developed for preparation of a porphyrin based covalent organic polymer (PoTz-COP). A tetra-norbornene functional porphyrin is chosen as the core and a bis-tetrazine as the linker. The PoTz-COP is readily formed by just mixing the components without a catalyst and under mild conditions. Chemical structure, morphology (XRD, SEM-EDX), porosity (BET), thermal stability (TGA), optical and gas sorption (CO2 uptake) and selectivity (CO2/N2) properties via Myers and Prausnitz's ideal adsorbed solution theory (IAST) are investigated. PoTz-COP shows remarkably high adsorption selectivity of CO2 over N2 as found 80, 42, and 47 at 50/50 ratio; 84, 39 and 40 at 15/85 ratio; and 84, 39 and 38 at 05/95 ratio at temperatures of 273 K, 298 K and 320 K at 1.1 bar pressure respectively. The optical band gap is determined relatively narrow as 1.66 eV.

KW - Covalent organic polymer

KW - Gas sorption

KW - Inverse electron demand Diels-Alder reaction

KW - Selectivity

KW - Tetrazine

UR - http://www.scopus.com/inward/record.url?scp=85111009780&partnerID=8YFLogxK

U2 - 10.1016/j.eurpolymj.2021.110664

DO - 10.1016/j.eurpolymj.2021.110664

M3 - Article

AN - SCOPUS:85111009780

SN - 0014-3057

VL - 157

JO - European Polymer Journal

JF - European Polymer Journal

M1 - 110664

ER -

Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

Abstract

Bibliographical note

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this