Photoswitching of Local (Anti)Aromaticity in Biphenylene-Based Diarylethene Molecular Switches

Funding Agencies|Hungarian Academy of Sciences through the Lendulet Program [LENDULET_2018_355]; National Research, Development and Innovation Office, Hungary (NKFIH Grant) [FK 123760]; Olle Engkvist Foundation [184-568, 204-0183]; Swedish Research Council [2019-03664]; AForsk [20-570]; Carl Trygger Foundation [CTS 20:102]; New National Excellence Program of the Ministry for Innovation and Technology from the Source of the National Research, Development and Innovation Fund [UNKP-21-2]; Ministry of Innovation and Technology from the National Research, Development and Innovation Fund
Photoinduced tuning of (anti)aromaticity and associated molecular properties is currently in the focus of attention for both tailoring photochemical reactivity and designing new materials. Here, we report on the synthesis and spectroscopic characterization of diarylethene-based molecular switches embedded in a biphenylene structure composed of rings with different levels of local (anti)aromaticity. We show that it is possible to modulate and control the (anti)aromatic character of each ring through reversible photoswitching of the aryl units of the system between open and closed forms. Remarkably, it is shown that the irreversible formation of an annulated bis(dihydro-thiopyran) side-product that hampers the photoswitching can be efficiently suppressed when the aryl core formed by thienyl groups in one switch is replaced by thiazolyl groups in another.

Mayer, Peter J.Res Ctr Nat Sci, Hungary; Univ Szeged, Hungary (författare)
Gazdag, TamasRes Ctr Nat Sci, Hungary; Eotvos Lorand Univ, Hungary (författare)
Demeter, AttilaRes Ctr Nat Sci, Hungary (författare)
Oruganti, BaswanthLinnéuniversitetet,Institutionen för kemi och biomedicin (KOB),Linnaeus Univ, Sweden(Swepub:lnu)baoraa (författare)
Durbeej, BoLinköpings universitet,Bioinformatik,Tekniska fakulteten(Swepub:liu)bodu88 (författare)
London, GaborRes Ctr Nat Sci, Hungary (författare)
Res Ctr Nat Sci, HungaryRes Ctr Nat Sci, Hungary; Univ Szeged, Hungary (creator_code:org_t)

Ingår i:Journal of Organic Chemistry: American Chemical Society (ACS)87:15, s. 9532-95420022-32631520-6904

Av författaren/redakt...: Kalapos, Peter P ...; Mayer, Peter J.; Gazdag, Tamas; Demeter, Attila; Oruganti, Baswan ...; Durbeej, Bo; visa fler...; London, Gabor; visa färre...

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