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

Affiliation
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
Kingsbury, Christopher J.;
ORCID
0000-0001-5665-7456
Affiliation
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
Kielmann, Marc;
Affiliation
School of Chemistry, Trinity College Dublin, The University of Dublin, 2 Dublin, Ireland
Twamley, Brendan;
ORCID
0000-0002-7467-1654
Affiliation
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
Senge, Mathias O.

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.

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