1401464-90-1

Basic information

• Product Name: 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile
• Synonyms: 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile
• CAS NO: 1401464-90-1
• Molecular Weight: 280.329
• Mol File: 1401464-90-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile(1401464-90-1)
• EPA Substance Registry System: 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile(1401464-90-1)

Safety Data

• Hazardous Substances Data: 1401464-90-1(Hazardous Substances Data)

Upstream product

• 298212-99-4 2-(4-iodophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1401464-89-8 2-[4-(triisopropylsilylethynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 75883-03-3 4'-(2-trimethylsilylethynyl)acetophenone 
• 1401464-92-3 2-{(2-cyclohepta-2,4,6-trienyl)-1-[4-(trimethylsilylethynyl)phenyl]ethylidene}malononitrile 
• 1401464-93-4 2-[(4-(trimethylsilylethynyl)phenyl)]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1401464-94-5 C₂₀H₁₁AgN₂ 
• 1401465-05-1 C₂₀H₁₂N₂ 

Downstream Products

• 1401464-84-3 C₉₈H₃₁N₃O 
• 1401464-95-6 C₁₀₀H₃₁N₃O 
• 1401464-96-7 2-(4'-bromoethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1401465-05-1 C₂₀H₁₂N₂ 
• 1448895-07-5 2-[4-(trimethylsilyl-1,3-butadiynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1448895-06-4 2-[4-(1,3-butadiynyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1582783-78-5 2-(4-(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)phenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1582783-83-2 C₂₇H₁₉N₅ 

Relevant articles and documents

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.

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.