Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films

Publication type:
Journal article
Metadata:
Autoren
  • Giuseppe Bengasi
  • Jessica SS Desport
  • Kamal Baba
  • Joao P Cosas Fernandes
  • Olivier De Castro
  • Katja Heinze
  • Nicolas DD Boscher
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000517310200035&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1039/c9ra09711b
eISSN
2046-2069
Externe Identifier
  • Clarivate Analytics Document Solution ID: KR0KS
  • PubMed Identifier: 35493879
Ausgabe der Veröffentlichung
12
Zeitschrift
RSC ADVANCES
Paginierung
7048 - 7057
Datum der Veröffentlichung
2020
Status
Published
Titel
Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films
Sub types
  • Article
Ausgabe der Zeitschrift
10

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<p>This work reports the strong correlation between the conductivity of fused porphyrins thin films and the porphyrin substituents.</p>
Autoren
  • Giuseppe Bengasi
  • Jessica S Desport
  • Kamal Baba
  • João P Cosas Fernandes
  • Olivier De Castro
  • Katja Heinze
  • Nicolas D Boscher
DOI
10.1039/c9ra09711b
eISSN
2046-2069
Ausgabe der Veröffentlichung
12
Zeitschrift
RSC Advances
Sprache
en
Online publication date
2020
Paginierung
7048 - 7057
Status
Published online
Herausgeber
Royal Society of Chemistry (RSC)
Herausgeber URL
http://dx.doi.org/10.1039/c9ra09711b
Datum der Datenerfassung
2024
Titel
Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films
Ausgabe der Zeitschrift
10

Data source: Crossref

Abstract
The straightforward synthesis of directly fused porphyrins (porphyrin tapes) from 5,15-diphenyl porphyrinato nickel(ii) complexes with different substituents on the phenyl rings is achieved while processing from the gas phase. The porphyrin tapes, exhibiting NIR absorption, are readily obtained in thin film form. The gas phase approach cuts the need for solubilizing groups allowing for the first time the study of their conductivity according to the substituent. 2-Point probe and conductivity AFM measurements evidence that reducing the size of the <i>meso</i> substituents, phenyl < mesityl < di(3,5-<i>tert</i>-butyl)phenyl < di(2,6-dodecyloxy)phenyl, improves the thin film conductivity by several orders of magnitude. Density functional theory and gel permeation chromatography, correlate this improvement to changes in the intermolecular distances and molecular geometry. Furthermore, the oCVD of porphyrins with free <i>ortho</i>-phenyl positions causes intramolecular dehydrogenative side reactions inducing a complete planarization of the molecule. This molecular flattening drastically affects the π-π stacking between the porphyrins further enhancing the electronic properties of the films.
Addresses
  • Materials Research and Technology, Luxembourg Institute of Science and Technology (LIST) 5 Avenue des Hauts-Fourneaux L-4362 Esch/Alzette Luxembourg nicolas.boscher@list.lu.
Autoren
  • Giuseppe Bengasi
  • Jessica S Desport
  • Kamal Baba
  • João P Cosas Fernandes
  • Olivier De Castro
  • Katja Heinze
  • Nicolas D Boscher
DOI
10.1039/c9ra09711b
eISSN
2046-2069
Externe Identifier
  • PubMed Identifier: 35493879
  • PubMed Central ID: PMC9049719
Funding acknowledgements
  • Fonds National de la Recherche Luxembourg: POLYPORPH (C15/MS/10340560/POLYPORH/Boscher)
Open access
true
ISSN
2046-2069
Ausgabe der Veröffentlichung
12
Zeitschrift
RSC advances
Sprache
eng
Medium
Electronic-eCollection
Online publication date
2020
Open access status
Open Access
Paginierung
7048 - 7057
Datum der Veröffentlichung
2020
Status
Published
Publisher licence
CC BY-NC
Datum der Datenerfassung
2022
Titel
Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films.
Sub types
  • research-article
  • Journal Article
Ausgabe der Zeitschrift
10

Files

https://pubs.rsc.org/en/content/articlepdf/2020/ra/c9ra09711b https://europepmc.org/articles/PMC9049719?pdf=render

Data source: Europe PubMed Central

Abstract
The straightforward synthesis of directly fused porphyrins (porphyrin tapes) from 5,15-diphenyl porphyrinato nickel(ii) complexes with different substituents on the phenyl rings is achieved while processing from the gas phase. The porphyrin tapes, exhibiting NIR absorption, are readily obtained in thin film form. The gas phase approach cuts the need for solubilizing groups allowing for the first time the study of their conductivity according to the substituent. 2-Point probe and conductivity AFM measurements evidence that reducing the size of the meso substituents, phenyl < mesityl < di(3,5-tert-butyl)phenyl < di(2,6-dodecyloxy)phenyl, improves the thin film conductivity by several orders of magnitude. Density functional theory and gel permeation chromatography, correlate this improvement to changes in the intermolecular distances and molecular geometry. Furthermore, the oCVD of porphyrins with free ortho-phenyl positions causes intramolecular dehydrogenative side reactions inducing a complete planarization of the molecule. This molecular flattening drastically affects the π-π stacking between the porphyrins further enhancing the electronic properties of the films.
Date of acceptance
2020
Autoren
  • Giuseppe Bengasi
  • Jessica S Desport
  • Kamal Baba
  • João P Cosas Fernandes
  • Olivier De Castro
  • Katja Heinze
  • Nicolas D Boscher
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/35493879
DOI
10.1039/c9ra09711b
eISSN
2046-2069
Externe Identifier
  • PubMed Central ID: PMC9049719
Ausgabe der Veröffentlichung
12
Zeitschrift
RSC Adv
Sprache
eng
Country
England
Paginierung
7048 - 7057
PII
c9ra09711b
Datum der Veröffentlichung
2020
Status
Published online
Titel
Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
10

Data source: PubMed

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