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A twisted bay-substituted quaterrylene phosphorescing in the NIR spectral region

Miletiić, Tanja, Fermi, Andrea, Papadakis, Ioannis, Orfanos, Ioannis, Karampitsos, Nikolaos, Avramopoulos, Aggelos, Demitri, Nicola, De Leo, Federica, Pope, Simon J. A. ORCID:, Papadopoulos, Manthos G., Couris, Stelios and Bonifazi, Davide ORCID: 2017. A twisted bay-substituted quaterrylene phosphorescing in the NIR spectral region. Helvetica Chimica Acta 100 (11) , e1700192. 10.1002/hlca.201700192

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The preparation of the first soluble quaterrylene derivative featuring peripheral tert-butyl substituents and sterically hindering, core-anchored triflate groups has been achieved. This involves a facile synthetic route based on an oxidative coupling of perylene precursors in the presence of H2O2 as oxidant. The steric hindrance between the TfO substituents at the central bay position of the quaterrylene board triggers a strong deformation of the central perylene planarity, which forces the quaterrylene platform to adopt a twisted geometry as shown by X-ray analysis. Exceptionally, photophysical investigations show that the core-twisted quaterrylene phosphoresces in the NIR spectral region at 1716 nm. Moreover, third-order nonlinear optical measurements on solutions and thin film containing the relevant molecule showed very large second hyperpolarizability values, as predicted by theoretical calculations at the CAM-B3LYP/6-31G** level of theory, making this material very appealing for photonic applications.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley-Blackwell
ISSN: 0018-019X
Funders: Marie Sk�odowska-Curie Action-Research and Innovation Staff Exchange (RISE)
Date of First Compliant Deposit: 5 October 2017
Date of Acceptance: 19 September 2017
Last Modified: 05 Nov 2022 17:26

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