Imperial College London
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Dr Florian Glöcklhofer

Faculty of Natural Sciences, Department of Chemistry

Visiting Researcher
 
 
 
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Contact

 

f.glocklhofer Website

 
 
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Location

 

Molecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@unpublished{Pletzer:2021:10.12688/openreseurope.13723.1,
author = {Pletzer, M and Plasser, F and Rimmele, M and Heeney, M and Glöcklhofer, F},
doi = {10.12688/openreseurope.13723.1},
publisher = {F1000Research},
title = {[2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(pphenylene vinylene)s (PPVs)},
url = {http://dx.doi.org/10.12688/openreseurope.13723.1},
year = {2021}
}
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RIS format (EndNote, RefMan)

TY  - UNPB
AB  - Background: Poly(p-phenylene vinylene)s (PPVs) and [2.2.2.2]paracyclophanetetraene (PCT) are both composed of alternating π-conjugated para-phenylene and vinylene units. However, while the former constitute a class of π-conjugated polymers that has been used in organic electronics for decades, the latter is a macrocycle that only recently revealed its potential for applications such as organic battery electrodes. The cyclic structure endows PCT with unusual properties, and further tuning of these may be required for specific applications. Methods: In this article, we adopt an approach often used for tuning the properties of PPVs, the introduction of alkoxy (or alkylthio) substituents at the phenylene units, for tuning the optoelectronic properties of PCT. The resulting methoxy- and methylthio-substituted PCTs, obtained by Wittig cyclisation reactions, are studied by UV-vis absorption, photoluminescence, and cyclic voltammetry measurements, and investigated computationally using the visualisation of chemical shielding tensors (VIST) method. Results: The measurements show that substitution leads to slight changes in terms of absorption/emission energies and redox potentials while having a pronounced effect on the photoluminescence intensity. The computations show the effect of the substituents on the ring currents and chemical shielding and on the associated local and global (anti)aromaticity of the macrocycles, highlighting the interplay of local and global aromaticity in various electronic states. Conclusions: The study offers interesting insights into the tuneability of the properties of this versatile class of π-conjugated macrocycles.
AU  - Pletzer,M
AU  - Plasser,F
AU  - Rimmele,M
AU  - Heeney,M
AU  - Glöcklhofer,F
DO  - 10.12688/openreseurope.13723.1
PB  - F1000Research
PY  - 2021///
TI  - [2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(pphenylene vinylene)s (PPVs)
UR  - http://dx.doi.org/10.12688/openreseurope.13723.1
UR  - https://open-research-europe.ec.europa.eu/articles/1-111/v1
UR  - http://hdl.handle.net/10044/1/99293
ER  -
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