Multi-Photochromic Molecules Based on Dihydroazulene Units
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Multi-Photochromic Molecules Based on Dihydroazulene Units. / Petersen, Anne Ugleholdt; Kirschner Solberg Hansen, Jonathan; Sperling Andreasen, Emilie; Peder Christensen, Søren; Tolstrup, Anders; Bo Skov, Anders; Vlasceanu, Alexandru; Cacciarini, Martina; Brøndsted Nielsen, Mogens.
I: Chemistry - A European Journal, Bind 26, Nr. 59, 2020, s. 13419-13428.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Multi-Photochromic Molecules Based on Dihydroazulene Units
AU - Petersen, Anne Ugleholdt
AU - Kirschner Solberg Hansen, Jonathan
AU - Sperling Andreasen, Emilie
AU - Peder Christensen, Søren
AU - Tolstrup, Anders
AU - Bo Skov, Anders
AU - Vlasceanu, Alexandru
AU - Cacciarini, Martina
AU - Brøndsted Nielsen, Mogens
PY - 2020
Y1 - 2020
N2 - Multi-photochromic systems incorporating individually addressable switching units are attractive for development of advanced data storage devices. Here, we present the synthesis and properties of a selection of such molecular systems incorporating the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The influence of the linker (meta-phenylene vs. azulene-1,3-diyl vs. thiophene-2,5-diyl) separating two DHA units on the switching properties was investigated. An azulene-1,3-diyl spacer largely inhibited both the DHA-to-VHF photoisomerizations and the thermal VHF-to-DHA back-reactions; the latter occurred ten times slower than for the related compound with a meta-phenylene spacer. A DHA trimer containing three DHA units around a central benzene ring was found to undergo stepwise DHA-to-VHF photoisomerizations, whereas the thermal back-reactions occurred at similar rates for the three VHF entities. A meta-phenylene-bridged DHA dimer was subjected to further structural modifications at position C-1 of each DHA, having strong implications for the switching events, and synthetic steps for further functionalizations at position C-7 of each DHA were investigated. Finally, the molecular structure (from X-ray crystallographic analysis) between the meta-phenylene-bridged DHA dimer and CuI is presented.
AB - Multi-photochromic systems incorporating individually addressable switching units are attractive for development of advanced data storage devices. Here, we present the synthesis and properties of a selection of such molecular systems incorporating the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The influence of the linker (meta-phenylene vs. azulene-1,3-diyl vs. thiophene-2,5-diyl) separating two DHA units on the switching properties was investigated. An azulene-1,3-diyl spacer largely inhibited both the DHA-to-VHF photoisomerizations and the thermal VHF-to-DHA back-reactions; the latter occurred ten times slower than for the related compound with a meta-phenylene spacer. A DHA trimer containing three DHA units around a central benzene ring was found to undergo stepwise DHA-to-VHF photoisomerizations, whereas the thermal back-reactions occurred at similar rates for the three VHF entities. A meta-phenylene-bridged DHA dimer was subjected to further structural modifications at position C-1 of each DHA, having strong implications for the switching events, and synthetic steps for further functionalizations at position C-7 of each DHA were investigated. Finally, the molecular structure (from X-ray crystallographic analysis) between the meta-phenylene-bridged DHA dimer and CuI is presented.
KW - azulenes
KW - multistates
KW - photoswitches
KW - thermoswitches
KW - trimers
U2 - 10.1002/chem.202000530
DO - 10.1002/chem.202000530
M3 - Journal article
C2 - 32092209
AN - SCOPUS:85089005259
VL - 26
SP - 13419
EP - 13428
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 59
ER -
ID: 260400866