Header

UZH-Logo

Maintenance Infos

Subphthalocyanine-triangulene dyads: Property tuning for light-harvesting device applications


Rasmussen, Mads Georg; Jespersen, Malte Frydenlund; Blacque, Olivier; Mikkelsen, Kurt V; Juricek, Michal; Nielsen, Mogens Brøndsted (2022). Subphthalocyanine-triangulene dyads: Property tuning for light-harvesting device applications. WIREs Forensic Science, 10(5):1752-1762.

Abstract

Organic photovoltaics relies on the development of stable chromophores and redox-active organic molecules with tailor-made HOMO/LUMO energies. Here, we present the synthesis and properties of novel dyads composed of boron subphthalocyanine (SubPc) and triangulene units, connected either at the peripheral position of the subphthalocyanine or at the axial boron. The connectivity has strong implications for the absorption and fluorescence properties of the dyads, as well as their redox properties. While the SubPc unit has a bowl shape, triangulene is a planar structural unit that allows dyads to dimerize in the solid state on account of π-stacking interactions as shown by X-ray crystallography of one of the dyads. The electronic properties were also studied computationally by density functional theory methods. Excellent agreement between experimental and computed data were obtained, showing that our computational method is a strong tool in the rational design of optimum molecules to ultimately obtain finely tuned molecules for device applications.

Keywords: chromophores; conjugation; molecular engineering; redox‐active molecules; structure–property relationships

Abstract

Organic photovoltaics relies on the development of stable chromophores and redox-active organic molecules with tailor-made HOMO/LUMO energies. Here, we present the synthesis and properties of novel dyads composed of boron subphthalocyanine (SubPc) and triangulene units, connected either at the peripheral position of the subphthalocyanine or at the axial boron. The connectivity has strong implications for the absorption and fluorescence properties of the dyads, as well as their redox properties. While the SubPc unit has a bowl shape, triangulene is a planar structural unit that allows dyads to dimerize in the solid state on account of π-stacking interactions as shown by X-ray crystallography of one of the dyads. The electronic properties were also studied computationally by density functional theory methods. Excellent agreement between experimental and computed data were obtained, showing that our computational method is a strong tool in the rational design of optimum molecules to ultimately obtain finely tuned molecules for device applications.

Keywords: chromophores; conjugation; molecular engineering; redox‐active molecules; structure–property relationships

Statistics

Citations

Dimensions.ai Metrics
3 citations in Web of Science®
3 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

10 downloads since deposited on 10 Jan 2023
4 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Safety, Risk, Reliability and Quality
Physical Sciences > General Energy
Uncontrolled Keywords:chromophores, conjugation, molecular engineering, redox-active molecules, structure– property relationships
Language:English
Date:1 May 2022
Deposited On:10 Jan 2023 14:18
Last Modified:28 Apr 2024 01:43
Publisher:Wiley Open Access
ISSN:2573-9468
OA Status:Green
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/ese3.1071
PubMed ID:35909459
Project Information:
  • : FunderH2020
  • : Grant ID716139
  • : Project TitleINSPIRAL - Spin-Delocalization with a Twist: Chiral Open-Shell Helices
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)