Optoelectronic Molecular Switches Based on Dihydroazulene‐Vinylheptafulvene (DHA‐VHF)

Mrozek, Thomas; Ajayaghosh, Ayyappanpillai; Daub, Jörg

doi:10.1002/3527600329.ch3

Cited by 22 publications

(11 citation statements)

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“…The most extensively used families of photochromic compounds are (Figure 8.2) diarylethenes [56], fulgides [57], spiropyrans [20b], azobenzenes [58], dihydroazulenes [59], and flavylium compounds [60]. Only two families, furylfulgide and diarylethene derivatives, are P-type compounds.…”

Section: Energy Stimulationmentioning

confidence: 99%

Bistable and Multistable Systems

Balzani

Venturi

2008

Molecular Devices and Machines

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Section: Energy Stimulationmentioning

confidence: 99%

Bistable and Multistable Systems

Balzani

Venturi

2008

Molecular Devices and Machines

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“…This photochromic couple represents the most advanced organic system for MOST, although there are still challenges with this system to be solved. Another encouraging candidate for MOST is represented by the 2-phenyl-1,8a-dihydroazulene/vinylheptafulvene (DHA-Ph/VHF-Ph) couple (Figure 1, top box), which was first extensively studied by Daub and co-workers [17], and in the past decade by us [8]; this couple is the focus of this work. DHA-Ph has a characteristic absorption maximum at 360 nm in toluene and undergoes an electrocyclic light-induced ring-opening reaction to quantitatively form VHF-Ph (absorption onset 454 nm in toluene), with generally quite high quantum yield (60% in toluene).…”

Section: Introductionmentioning

confidence: 99%

ortho-Substituted 2-Phenyldihydroazulene Photoswitches: Enhancing the Lifetime of the Photoisomer by ortho-Aryl Interactions

et al. 2021

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Photochromic molecules are systems that undergo a photoisomerization to high-energy isomers and are attractive for the storage of solar energy in a closed-energy cycle, for example, in molecular solar thermal energy storage systems. One challenge is to control the discharge time of the high-energy isomer. Here, we show that different substituents in the ortho position of a phenyl ring at C-2 of dihydroazulene (DHA-Ph) significantly increase the half-life of the metastable vinylheptafulvene (VHF-Ph) photoisomer; thus, the energy-releasing VHF-to-DHA back-reaction rises from minutes to days in comparison to the corresponding para- and meta-substituted systems. Systems with two photochromic DHA-Ph units connected by a diacetylene bridge either at the para, meta and ortho positions and corresponding to a linear or to a cross-conjugated pathway between the two photochromes are also presented. Here, the ortho substitution was found to compromise the switching properties. Thus, irradiation of ortho-bridged DHA-DHA resulted in degradation, probably due to the proximity of the different functional groups that can give rise to side-reactions.

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“…The yellow dihydroazulene (DHA; 2-phenyl-1,8a-dihydroazulene-1,1-dicarbonitrile) 3 is a one-way photoswitch with a high quantum yield 4 of photoisomerization. Upon irradiation at its lowest-energy absorption maximum ( ca.…”

Section: Introductionmentioning

confidence: 99%