Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad. / Dowds, Mathias; Stenspil, Stine G.; de Souza, Joao H.; Laursen, Bo W.; Cacciarini, Martina; Nielsen, Mogens Brondsted.

I: ChemPhotoChem, Bind 6, Nr. 10, 202200152, 27.07.2022.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Dowds, M, Stenspil, SG, de Souza, JH, Laursen, BW, Cacciarini, M & Nielsen, MB 2022, 'Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad', ChemPhotoChem, bind 6, nr. 10, 202200152. https://doi.org/10.1002/cptc.202200152

APA

Dowds, M., Stenspil, S. G., de Souza, J. H., Laursen, B. W., Cacciarini, M., & Nielsen, M. B. (2022). Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad. ChemPhotoChem, 6(10), [202200152]. https://doi.org/10.1002/cptc.202200152

Vancouver

Dowds M, Stenspil SG, de Souza JH, Laursen BW, Cacciarini M, Nielsen MB. Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad. ChemPhotoChem. 2022 jul. 27;6(10). 202200152. https://doi.org/10.1002/cptc.202200152

Author

Dowds, Mathias ; Stenspil, Stine G. ; de Souza, Joao H. ; Laursen, Bo W. ; Cacciarini, Martina ; Nielsen, Mogens Brondsted. / Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad. I: ChemPhotoChem. 2022 ; Bind 6, Nr. 10.

Bibtex

@article{ce2b7a3713b1427586cbfdfa0fee1245,
title = "Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad",
abstract = "Molecules comprised of two or more switches have potential to exist in a variety of states, which may only be accessible by a {"}correct{"} sequence of stimuli on account of the influence of the neighboring unit. Here we present a straightforward synthesis of a dyad incorporating two photoswitchable units, dihydroazulene (DHA) and spiropyran (SP). The photoswitching properties of both chromophores and the acido-triggered switching of the SP were retained in the dyad, allowing selective switching between eight states with distinct absorption and fluorescence properties (corresponding to light-controlled fluorescence on/off switching). Photoisomerization of DHA and protonation of SP allowed an orthogonal control of the individual sites. Conversely, photoisomerization of SP to its merocyanine (MC) isomer could not be performed without also addressing DHA-to-vinylheptafulvene (VHF) switching. Access to the DHA-MC state thus appeared to be path-dependent as it could exclusively be reached by deprotonation of the thermally stable DHA-E-MCH.",
keywords = "dihydroazulene, electrocyclic reactions, fluorescence, photochromism, spiropyran, PHOTOCHROMISM, TEMPERATURE, SOLVENT, SWITCH",
author = "Mathias Dowds and Stenspil, {Stine G.} and {de Souza}, {Joao H.} and Laursen, {Bo W.} and Martina Cacciarini and Nielsen, {Mogens Brondsted}",
year = "2022",
month = jul,
day = "27",
doi = "10.1002/cptc.202200152",
language = "English",
volume = "6",
journal = "ChemPhotoChem",
issn = "2367-0932",
publisher = "Wiley-VCH",
number = "10",

}

RIS

TY - JOUR

T1 - Orthogonal- and Path-Dependent Photo/Acidoswitching in an Eight-State Dihydroazulene-Spiropyran Dyad

AU - Dowds, Mathias

AU - Stenspil, Stine G.

AU - de Souza, Joao H.

AU - Laursen, Bo W.

AU - Cacciarini, Martina

AU - Nielsen, Mogens Brondsted

PY - 2022/7/27

Y1 - 2022/7/27

N2 - Molecules comprised of two or more switches have potential to exist in a variety of states, which may only be accessible by a "correct" sequence of stimuli on account of the influence of the neighboring unit. Here we present a straightforward synthesis of a dyad incorporating two photoswitchable units, dihydroazulene (DHA) and spiropyran (SP). The photoswitching properties of both chromophores and the acido-triggered switching of the SP were retained in the dyad, allowing selective switching between eight states with distinct absorption and fluorescence properties (corresponding to light-controlled fluorescence on/off switching). Photoisomerization of DHA and protonation of SP allowed an orthogonal control of the individual sites. Conversely, photoisomerization of SP to its merocyanine (MC) isomer could not be performed without also addressing DHA-to-vinylheptafulvene (VHF) switching. Access to the DHA-MC state thus appeared to be path-dependent as it could exclusively be reached by deprotonation of the thermally stable DHA-E-MCH.

AB - Molecules comprised of two or more switches have potential to exist in a variety of states, which may only be accessible by a "correct" sequence of stimuli on account of the influence of the neighboring unit. Here we present a straightforward synthesis of a dyad incorporating two photoswitchable units, dihydroazulene (DHA) and spiropyran (SP). The photoswitching properties of both chromophores and the acido-triggered switching of the SP were retained in the dyad, allowing selective switching between eight states with distinct absorption and fluorescence properties (corresponding to light-controlled fluorescence on/off switching). Photoisomerization of DHA and protonation of SP allowed an orthogonal control of the individual sites. Conversely, photoisomerization of SP to its merocyanine (MC) isomer could not be performed without also addressing DHA-to-vinylheptafulvene (VHF) switching. Access to the DHA-MC state thus appeared to be path-dependent as it could exclusively be reached by deprotonation of the thermally stable DHA-E-MCH.

KW - dihydroazulene

KW - electrocyclic reactions

KW - fluorescence

KW - photochromism

KW - spiropyran

KW - PHOTOCHROMISM

KW - TEMPERATURE

KW - SOLVENT

KW - SWITCH

U2 - 10.1002/cptc.202200152

DO - 10.1002/cptc.202200152

M3 - Journal article

VL - 6

JO - ChemPhotoChem

JF - ChemPhotoChem

SN - 2367-0932

IS - 10

M1 - 202200152

ER -

ID: 315768588