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Article

Self-Organization of Porphyrin–POM Dyads: Nonplanar Diacids and Oxoanions in Low-Dimensional H-Bonding Networks

by
Christopher J. Kingsbury
1,
Marc Kielmann
1,
Brendan Twamley
2 and
Mathias O. Senge
3,*
1
Trinity Biomedical Sciences Institute, School of Chemistry, Chair of Organic Chemistry, Trinity College Dublin, The University of Dublin, 152-160 Pearse St., 2 Dublin, Ireland
2
School of Chemistry, Trinity College Dublin, The University of Dublin, 2 Dublin, Ireland
3
Focus Group—Molecular and Interfacial Engineering of Organic Nanosystems, Institute for Advanced Study (TUM-IAS), Technical University of Munich, Lichtenberg-Str. 2a, 85748 Garching, Germany
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(20), 7060; https://doi.org/10.3390/molecules27207060
Submission received: 3 October 2022 / Revised: 13 October 2022 / Accepted: 14 October 2022 / Published: 19 October 2022
(This article belongs to the Section Molecular Structure)
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Abstract

Coordinating the spatial arrangement of electroactive partners is crucial to designable molecular electronics and photonics. Porphyrins are ubiquitous reaction centers in nature; synthetic porphyrins, in the crystallographic solid state, are often coerced into monolithic stacks, inhibiting reactivity. Using the principles of self-organization, and by exploiting charge-balance principles, we can manipulate nonplanar porphyrins into one- and two-dimensional hydrogen-bonded polymers, with polyoxometalate (POM) and bifunctional counter-anions serving as linkers. Herein, we report 11 crystal structures as a systematic study of the interactions between dodecasubstituted porphyrin acids and nonstandard counterions, as well as the induced conformations in the porphyrin core. We can show that this hydrogen bond chelate is a viable method of organizing electroactive centers into filaments and monolayers for surface deposition and ultrathin devices.
Keywords: supramolecular chemistry; porphyrins; crystallography; polyoxometalates (POMs); molecular engineering supramolecular chemistry; porphyrins; crystallography; polyoxometalates (POMs); molecular engineering
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MDPI and ACS Style

Kingsbury, C.J.; Kielmann, M.; Twamley, B.; Senge, M.O. Self-Organization of Porphyrin–POM Dyads: Nonplanar Diacids and Oxoanions in Low-Dimensional H-Bonding Networks. Molecules 2022, 27, 7060. https://doi.org/10.3390/molecules27207060

AMA Style

Kingsbury CJ, Kielmann M, Twamley B, Senge MO. Self-Organization of Porphyrin–POM Dyads: Nonplanar Diacids and Oxoanions in Low-Dimensional H-Bonding Networks. Molecules. 2022; 27(20):7060. https://doi.org/10.3390/molecules27207060

Chicago/Turabian Style

Kingsbury, Christopher J., Marc Kielmann, Brendan Twamley, and Mathias O. Senge. 2022. "Self-Organization of Porphyrin–POM Dyads: Nonplanar Diacids and Oxoanions in Low-Dimensional H-Bonding Networks" Molecules 27, no. 20: 7060. https://doi.org/10.3390/molecules27207060

APA Style

Kingsbury, C. J., Kielmann, M., Twamley, B., & Senge, M. O. (2022). Self-Organization of Porphyrin–POM Dyads: Nonplanar Diacids and Oxoanions in Low-Dimensional H-Bonding Networks. Molecules, 27(20), 7060. https://doi.org/10.3390/molecules27207060

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