Light-actuated resorcin[4]arene cavitands

Víctor García-López; Jovana V. Milić; Michal Zalibera; Dmytro Neshchadin; Martin Kuss-Petermann; Laurent Ruhlmann; Julia Nomrowski; Nils Trapp; Corinne Boudon; Georg Gescheidt; Oliver S. Wenger; François Diederich

doi:10.1016/j.tet.2018.08.002

Light-actuated resorcin[4]arene cavitands

Víctor García-López, Jovana V. Milić, Michal Zalibera, Dmytro Neshchadin, Martin Kuss-Petermann, Laurent Ruhlmann, Julia Nomrowski, Nils Trapp, Corinne Boudon, Georg Gescheidt, Oliver S. Wenger, François Diederich^*

^*Corresponding author for this work

Institute of Physical and Theoretical Chemistry (6350)

Research output: Contribution to journal › Article › peer-review

Abstract

A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.

Original language	English
Pages (from-to)	5615-5626
Number of pages	12
Journal	Tetrahedron
Volume	74
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2018.08.002
Publication status	Published - 27 Sept 2018

Keywords

Light-actuated cavitands
Resorcin[4]arene switches
Ruthenium-based cavitands
Semiquinone radical anion

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2018.08.002

Cite this

@article{94d34811db6a4a6194fbec73676e2e01,

title = "Light-actuated resorcin[4]arene cavitands",

abstract = "A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.",

keywords = "Light-actuated cavitands, Resorcin[4]arene switches, Ruthenium-based cavitands, Semiquinone radical anion",

author = "V{\'i}ctor Garc{\'i}a-L{\'o}pez and Mili{\'c}, {Jovana V.} and Michal Zalibera and Dmytro Neshchadin and Martin Kuss-Petermann and Laurent Ruhlmann and Julia Nomrowski and Nils Trapp and Corinne Boudon and Georg Gescheidt and Wenger, {Oliver S.} and Fran{\c c}ois Diederich",

year = "2018",

month = sep,

day = "27",

doi = "10.1016/j.tet.2018.08.002",

language = "English",

volume = "74",

pages = "5615--5626",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "39",

}

TY - JOUR

T1 - Light-actuated resorcin[4]arene cavitands

AU - García-López, Víctor

AU - Milić, Jovana V.

AU - Zalibera, Michal

AU - Neshchadin, Dmytro

AU - Kuss-Petermann, Martin

AU - Ruhlmann, Laurent

AU - Nomrowski, Julia

AU - Trapp, Nils

AU - Boudon, Corinne

AU - Gescheidt, Georg

AU - Wenger, Oliver S.

AU - Diederich, François

PY - 2018/9/27

Y1 - 2018/9/27

N2 - A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.

AB - A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.

KW - Light-actuated cavitands

KW - Resorcin[4]arene switches

KW - Ruthenium-based cavitands

KW - Semiquinone radical anion

UR - http://www.scopus.com/inward/record.url?scp=85051741998&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.08.002

DO - 10.1016/j.tet.2018.08.002

M3 - Article

AN - SCOPUS:85051741998

SN - 0040-4020

VL - 74

SP - 5615

EP - 5626

JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -

Light-actuated resorcin[4]arene cavitands

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this