Reactivity of Nickel(II) Porphyrins in oCVD Processes-Polymerisation, Intramolecular Cyclisation and Chlorination

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Giuseppe Bengasi
  • Kamal Baba
  • Oliver Back
  • Gilles Frache
  • Katja Heinze
  • Nicolas D Boscher
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000474808200020&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/chem.201900793
eISSN
1521-3765
Externe Identifier
  • Clarivate Analytics Document Solution ID: IH9EA
  • PubMed Identifier: 30939219
ISSN
0947-6539
Ausgabe der Veröffentlichung
35
Zeitschrift
CHEMISTRY-A EUROPEAN JOURNAL
Schlüsselwörter
  • chemical vapor deposition
  • nickel
  • polymerization
  • porphyrins
  • thin films
Paginierung
8313 - 8320
Datum der Veröffentlichung
2019
Status
Published
Titel
Reactivity of Nickel(II) Porphyrins in oCVD Processes-Polymerisation, Intramolecular Cyclisation and Chlorination
Sub types
  • Article
Ausgabe der Zeitschrift
25

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title><jats:p>Oxidative chemical vapour deposition of (5,15‐diphenylporphyrinato)nickel(II) (NiDPP) with iron(III) chloride as oxidant yielded a conjugated poly(metalloporphyrin) as a highly coloured thin film, which is potentially useful for optoelectronic applications. This study clarified the reactive sites of the porphyrin monomer NiDPP by HRMS, UV/Vis/NIR spectroscopy, cyclic voltammetry and EPR spectroscopy in combination with quantum chemical calculations. Unsubstituted <jats:italic>meso</jats:italic> positions are essential for successful polymerisation, as demonstrated by varying the porphyrin <jats:italic>meso</jats:italic> substituent pattern from di‐ to tri‐ and tetraphenyl substitution. DFT calculations support the proposed radical oxidative coupling mechanism and explain the regioselectivity of the C−C coupling processes. Depositing the conjugated polymer on glass slides and on thermoplastic transparent polyethylene naphthalate demonstrated the suitability of the porphyrin material for flexible optoelectronic devices.</jats:p>
Autoren
  • Giuseppe Bengasi
  • Kamal Baba
  • Oliver Back
  • Gilles Frache
  • Katja Heinze
  • Nicolas D Boscher
DOI
10.1002/chem.201900793
eISSN
1521-3765
ISSN
0947-6539
Ausgabe der Veröffentlichung
35
Zeitschrift
Chemistry – A European Journal
Sprache
en
Online publication date
2019
Paginierung
8313 - 8320
Datum der Veröffentlichung
2019
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/chem.201900793
Datum der Datenerfassung
2023
Titel
Reactivity of Nickel(II) Porphyrins in oCVD Processes—Polymerisation, Intramolecular Cyclisation and Chlorination
Ausgabe der Zeitschrift
25

Datenquelle: Crossref

Abstract
Oxidative chemical vapour deposition of (5,15-diphenylporphyrinato)nickel(II) (NiDPP) with iron(III) chloride as oxidant yielded a conjugated poly(metalloporphyrin) as a highly coloured thin film, which is potentially useful for optoelectronic applications. This study clarified the reactive sites of the porphyrin monomer NiDPP by HRMS, UV/Vis/NIR spectroscopy, cyclic voltammetry and EPR spectroscopy in combination with quantum chemical calculations. Unsubstituted meso positions are essential for successful polymerisation, as demonstrated by varying the porphyrin meso substituent pattern from di- to tri- and tetraphenyl substitution. DFT calculations support the proposed radical oxidative coupling mechanism and explain the regioselectivity of the C-C coupling processes. Depositing the conjugated polymer on glass slides and on thermoplastic transparent polyethylene naphthalate demonstrated the suitability of the porphyrin material for flexible optoelectronic devices.
Addresses
  • Institute of Inorganic Chemistry and Analytical Chemistry, Johannes Gutenberg University of Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Autoren
  • Giuseppe Bengasi
  • Kamal Baba
  • Oliver Back
  • Gilles Frache
  • Katja Heinze
  • Nicolas D Boscher
DOI
10.1002/chem.201900793
eISSN
1521-3765
Externe Identifier
  • PubMed Identifier: 30939219
  • PubMed Central ID: PMC6771558
Funding acknowledgements
  • Fonds National de la Recherche Luxembourg: POLYPORH
Open access
true
ISSN
0947-6539
Ausgabe der Veröffentlichung
35
Zeitschrift
Chemistry (Weinheim an der Bergstrasse, Germany)
Sprache
eng
Medium
Print-Electronic
Online publication date
2019
Open access status
Open Access
Paginierung
8313 - 8320
Datum der Veröffentlichung
2019
Status
Published
Publisher licence
CC BY-NC-ND
Datum der Datenerfassung
2019
Titel
Reactivity of Nickel(II) Porphyrins in oCVD Processes-Polymerisation, Intramolecular Cyclisation and Chlorination.
Sub types
  • research-article
  • Journal Article
Ausgabe der Zeitschrift
25

Files

https://europepmc.org/articles/PMC6771558?pdf=render

Datenquelle: Europe PubMed Central

Abstract
Oxidative chemical vapour deposition of (5,15-diphenylporphyrinato)nickel(II) (NiDPP) with iron(III) chloride as oxidant yielded a conjugated poly(metalloporphyrin) as a highly coloured thin film, which is potentially useful for optoelectronic applications. This study clarified the reactive sites of the porphyrin monomer NiDPP by HRMS, UV/Vis/NIR spectroscopy, cyclic voltammetry and EPR spectroscopy in combination with quantum chemical calculations. Unsubstituted meso positions are essential for successful polymerisation, as demonstrated by varying the porphyrin meso substituent pattern from di- to tri- and tetraphenyl substitution. DFT calculations support the proposed radical oxidative coupling mechanism and explain the regioselectivity of the C-C coupling processes. Depositing the conjugated polymer on glass slides and on thermoplastic transparent polyethylene naphthalate demonstrated the suitability of the porphyrin material for flexible optoelectronic devices.
Autoren
  • Giuseppe Bengasi
  • Kamal Baba
  • Oliver Back
  • Gilles Frache
  • Katja Heinze
  • Nicolas D Boscher
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/30939219
DOI
10.1002/chem.201900793
eISSN
1521-3765
Externe Identifier
  • PubMed Central ID: PMC6771558
Funding acknowledgements
  • Fonds National de la Recherche Luxembourg: POLYPORH
Ausgabe der Veröffentlichung
35
Zeitschrift
Chemistry
Schlüsselwörter
  • chemical vapor deposition
  • nickel
  • polymerization
  • porphyrins
  • thin films
Sprache
eng
Country
Germany
Paginierung
8313 - 8320
Datum der Veröffentlichung
2019
Status
Published
Titel
Reactivity of Nickel(II) Porphyrins in oCVD Processes-Polymerisation, Intramolecular Cyclisation and Chlorination.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
25

Datenquelle: PubMed

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