102780-24-5

Upstream product

• 29647-95-8 2-(cyclohepta-2,4,6-trienyl)-1-phenylethan-1-one 
• 98-88-4 benzoyl chloride 
• 102780-13-2 2-phenyl-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 
• 102780-19-8 3-Methoxy-2-phenyl-3,8a-dihydro-2H-azulene-1,1-dicarbonitrile 
• 116263-45-7 <2-(2,4,6-Cycloheptatrien-1-yl)-1-phenylethyliden>propandinitril 

Downstream Products

• 102780-13-2 2-phenyl-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1173928-39-6 2-phenylazulene-1,3-dicarbonitrile 

Relevant academic research and scientific papers

Dihydroazulene/Vinylheptafulvene Photoswitch: Ultrafast Back Reaction Induced by Dihydronaphthalene Annulation

The vinylheptafulvene (VHF) to dihydroazulene (DHA) electrocyclization is known to proceed from an s-cis conformation of VHF and cannot occur from the more stable s-trans conformation. Locking the VHF in the s-cis conformation by the introduction of a dih

Photoswitchable dihydroazulene macrocycles for solar energy storage: The effects of ring strain

Efficient energy storage and release are two major challenges of solar energy harvesting technologies. The development of molecular solar thermal systems presents one approach to address these issues by tuning the isomerization reactions of photo/ thermos

Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates

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.

Evaluating Dihydroazulene/Vinylheptafulvene Photoswitches for Solar Energy Storage Applications

Efficient solar energy storage is a key challenge in striving toward a sustainable future. For this reason, molecules capable of solar energy storage and release through valence isomerization, for so-called molecular solar thermal energy storage (MOST), h

Reversible Multicolor Photochromism of Dihydroazulene Crystals

The photochemical conversion of 1,8a-dihydroazulene-1,1-dicarbonitrile (DHA) to vinylheptafulvene (VHF) is a positive T-type photoswitch that is well understood in solution, but has not been explored in the solid state. Upon excitation with UV light, DHA

Expanding the Hammett Correlations for the Vinylheptafulvene Ring-Closure Reaction

A selection of 2,3-diarylated photochromic dihydroazulenes (DHAs) was prepared by following two different protocols. The first protocol relies on the synthesis of a 3-bromo-substituted dihydroazulene, which is subjected to a Suzuki cross-coupling reaction

An effective trigger for energy release of vinylheptafulvene-based solar heat batteries

Stoichiometric copper(i) tetrakis(acetonitrile) is found to activate the thermal ring-closure reaction of a series of high-energy vinylheptafulvene isomers to the corresponding low-energy and photoactive dihydroazulenes, allowing the release of energy upon request.

Multistate Switches: Ruthenium Alkynyl-Dihydroazulene/Vinylheptafulvene Conjugates

Multimode molecular switches incorporating distinct and independently addressable functional components have potential applications as advanced switches and logic gates for molecular electronics and memory storage devices. Herein, we describe the synthesis and characterization of four switches based on the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch pair functionalized with the ruthenium-based Cp?(dppe)Ru ([Ru?]) metal complex (dppe=1,2-bis(diphenylphosphino)ethane; Cp?=pentamethylcyclopentadienyl). The [Ru?]-DHA conjugates can potentially exist in six different states accessible by alternation between DHA/VHF, RuII/RuIII, and alkynyl/vinylidene, which can be individually stimulated by using light/heat, oxidation/reduction, and acid/base. Access to the full range of states was found to be strongly dependent on the electronic communication between the metal center and the organic photoswitch in these [Ru?]-DHA conjugates. Detailed electrochemical, spectroscopic (UV/Vis, IR, NMR), and X-ray crystallographic studies indeed reveal significant electronic interactions between the two moieties. When in direct conjugation, the ruthenium metal center was found to quench the photochemical ring-opening of DHA, which in one case could be restored by protonation or oxidation, allowing conversion to the VHF state.

On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.

Dihydroazulene-buckminsterfullerene conjugates

The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light-induced ring-opening reaction of DHA to its corresponding VHF. Thus, C60 was found to significantly quench this conversion when situated closely to the DHA unit.