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Gas phase transformation of fluorinated benzoporphyrins to porphyrin-embedded conical nanocarbons

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Title
Gas phase transformation of fluorinated benzoporphyrins to porphyrin-embedded conical nanocarbons
Author(s)
Dominik Lungerich; Jakob Felix Hitzenberger; Michael Ruppel; Tibor Döpper; Matthias Witt; Ivana Ivanovic-Burmazovic; Andreas Görling; Norbert Jux; Thomas Drewello
Subject
Buckybowls, ; C-F activation, ; Collision-induced dissociation, ; Mass spectrometry, ; Porphyrinoids
Publication Date
2020-09
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.26, no.53, pp.12180 - 12187
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.Geodesic nitrogen-containing graphene fragments are interesting candidates for various materials applications, but the available synthetic protocols, which are required to overcome the intrinsic strain energy during the formation of bowl-shaped skeletons, are often incompatible with heteroatom-embedded structures. In this mass spectrometry-based gas phase study, we present by means of collision-induced dissociation experiments and supported by density functional theory calculations, the first evidences for the formation of a porphyrin-embedded conical nanocarbon. Influences of metalation and functionalization of the utilized tetrabenzoporphyrins were investigated throughout, which resulted in different cyclization efficiencies, different ionization possibilities and a variation of the dissociation pathway. Our results suggest a concerted cyclization mechanism for the fjord -region HF-elimination, which supports a selective pathway towards bent nitrogen-containing graphene fragments
URI
https://pr.ibs.re.kr/handle/8788114/8489
DOI
10.1002/chem.202002638
ISSN
0947-6539
Appears in Collections:
Center for Nanomedicine (나노의학 연구단) > 1. Journal Papers (저널논문)
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