Synthesis and Redox and Photophysical Properties of Benzodifuran-Spiropyran Ensembles

Li, Hui; Ding, J.; Chen, Songjie; Beyer, C.; Liu, Shi-Xia; Wagenknecht, H. A.; Hauser, A.; Decurtins, Silvio (2013). Synthesis and Redox and Photophysical Properties of Benzodifuran-Spiropyran Ensembles. Chemistry - a European journal, 19(20), pp. 6459-6466. Wiley-VCH 10.1002/chem.201204043

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Two benzodifuran (BDF)-coupled spiropyran (SP) systems and their BDF reference compounds were obtained in good yields through HuisgenMeldalSharpless click chemistry and then subjected to investigation of their electrochemical and photophysical properties. In both SP and merocyanine (MC) forms of the coupled molecules, the BDF-based emission is quenched to around 1 of the quantum yield of emission from the BDF reference compounds. Based on electrochemical data, this quenching is attributed to oxidative electron-transfer quenching. Irradiation at 366nm results in ring opening to the MC forms of the BDF-coupled SP compounds and the SP reference compound with a quantum efficiency of about 50. The rate constants for the thermal ring closing are approximately 3.4x103s1. However, in the photostationary states the MC fractions of the coupled molecules are substantially lower than that of the reference SP compound, attributed to the observed acceleration of the ring-closing reaction upon irradiation. As irradiation at 366nm invariably also excites higher-energy transitions of the BDF units in the coupled compounds, the ring-opening reaction is accelerated relative to the SP reference, which results in lower MC fractions in the photostationary state. Reversible photochromism of these BDF-coupled SP compounds renders them promising in the field of molecular switches.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Li, Hui; Chen, Songjie; Liu, Shi-Xia and Decurtins, Silvio

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Gabriela Claudia Frei

Date Deposited:

12 Apr 2014 10:44

Last Modified:

08 Jan 2015 18:53

Publisher DOI:

10.1002/chem.201204043

Additional Information:

136ME Times Cited:1 Cited References Count:42

Uncontrolled Keywords:

asymmetric synthesis click chemistry electron transfer photochromism redox chemistry spiro compounds photochromic switches molecular switches nitrospiropyrans nanoparticles polymer photoprocesses fluorescence temperature storage cells

BORIS DOI:

10.7892/boris.46366

URI:

https://boris.unibe.ch/id/eprint/46366

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