Multistate Photoswitches:  Macrocyclic Dihydroazulene/Azobenzene Conjugates

Alexandru Vlasceanu; Mads Koerstz Madsen; Anders Bo Skov; Kurt Valentin Mikkelsen; Mogens Brøndsted Nielsen

doi:10.1002/anie.201712942

Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates

Alexandru Vlasceanu, Mads Koerstz Madsen, Anders Bo Skov, Kurt Valentin Mikkelsen, Mogens Brøndsted Nielsen

Kemisk Institut

17 Citationer (Scopus)

Abstract

Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ⟨000⟩, ⟨001⟩, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ⟨000⟩, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ⟨111⟩. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ⟨011⟩ to ultimately furnish ⟨000⟩. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.

Originalsprog	Engelsk
Tidsskrift	Angewandte Chemie International Edition
Vol/bind	57
Udgave nummer	21
Sider (fra-til)	6069-6072
Antal sider	4
ISSN	1433-7851
DOI	https://doi.org/10.1002/anie.201712942
Status	Udgivet - 22 maj 2018

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10.1002/anie.201712942

Citationsformater

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title = "Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates",

abstract = "Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ⟨000⟩, ⟨001⟩, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ⟨000⟩, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ⟨111⟩. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ⟨011⟩ to ultimately furnish ⟨000⟩. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.",

author = "Alexandru Vlasceanu and Madsen, {Mads Koerstz} and Skov, {Anders Bo} and Mikkelsen, {Kurt Valentin} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2018",

month = may,

day = "22",

doi = "10.1002/anie.201712942",

language = "English",

volume = "57",

pages = "6069--6072",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",

number = "21",

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TY - JOUR

T1 - Multistate Photoswitches

T2 - Macrocyclic Dihydroazulene/Azobenzene Conjugates

AU - Vlasceanu, Alexandru

AU - Madsen, Mads Koerstz

AU - Skov, Anders Bo

AU - Mikkelsen, Kurt Valentin

AU - Nielsen, Mogens Brøndsted

PY - 2018/5/22

Y1 - 2018/5/22

N2 - Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ⟨000⟩, ⟨001⟩, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ⟨000⟩, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ⟨111⟩. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ⟨011⟩ to ultimately furnish ⟨000⟩. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.

AB - Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ⟨000⟩, ⟨001⟩, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ⟨000⟩, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ⟨111⟩. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ⟨011⟩ to ultimately furnish ⟨000⟩. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.

U2 - 10.1002/anie.201712942

DO - 10.1002/anie.201712942

M3 - Journal article

C2 - 29566296

SN - 1433-7851

VL - 57

SP - 6069

EP - 6072

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 21

ER -

Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates

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