Oleszak C, Schol P, Ritterhoff C, Krug M, Martin M, Bo Y, Meyer B, Clark T, Guldi DM, Jux N (2024)
Publication Language: English
Publication Type: Journal article
Publication year: 2024
Book Volume: 63
Article Number: e202409363
Journal Issue: 48
A new clear-cut strategy for fusing N-heterocyclic and carbon-pure systems is introduced en route to a versatile platform of multi-purpose tetrapyrrolic chromophores. In particular, three novel C−C bond-fused porphyrin-hexabenzocoronene (HBC) conjugates were synthesized under oxidative cyclodehydrogenation conditions, starting from tailor-made nickel porphyrin precursors. The fusion of the individual aromatic systems via 5-membered rings led to highly soluble π-extended porphyrins in excellent yields. The resulting porphyrin-HBC conjugates exhibit absorption cross-sections that are of interdisciplinary interest in the ever-growing field of organic photovoltaics and near-infrared (NIR) dyes. Quantum chemical calculations show that the newly formed 5-membered rings induce biradicaloid character in the porphyrin core, which has a strong impact on excited state lifetimes. This is confirmed by a thorough optoelectronic and time-resolved characterization in order to understand these unique features better. Broadened absorption characteristics go hand-in-hand with short-lived excited states with up to six orders of magnitude faster decay rates.
APA:
Oleszak, C., Schol, P., Ritterhoff, C., Krug, M., Martin, M., Bo, Y.,... Jux, N. (2024). Fused Hexabenzocoronene-Porphyrin Conjugates with Tailorable Excited-State Lifetimes. Angewandte Chemie International Edition, 63(48). https://doi.org/10.1002/anie.202409363
MLA:
Oleszak, Christoph, et al. "Fused Hexabenzocoronene-Porphyrin Conjugates with Tailorable Excited-State Lifetimes." Angewandte Chemie International Edition 63.48 (2024).
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