688753-79-9

Usage

Uses

2,7-Diformyl-1,8-naphthalenediol can be used as catalysts.

Upstream product

• 172915-62-7 1,8-bis(methoxymethoxy)naphthalene 
• 569-42-6 1,8-dihydroxynaphthalene 

Downstream Products

• 1402835-20-4 C₃₄H₂₉NO₃ 
• 1402835-15-7 {2,7-di-[2,6-(3,5-di-methylphenylimino)methyl]-1,8-naphthalenediolato}-(Ni^II)2-(methyl)2(trimethylphosphine)2 
• 1005788-71-5 C₃₆H₄₂N₂O₂ 

Relevant academic research and scientific papers

A study of the competitive multiple hydrogen bonding effect and its associated excited-state proton transfer tautomerism

1,8-Dihydroxynaphthalene-2,7-dicarbaldehyde (DHDA) has been strategically designed and synthesized with the aim to study the competitive multiple hydrogen bonding (H-bonding) effect and the associated excited-state intramolecular proton transfer reaction (ESIPT). In nonpolar solvents such as cyclohexane, equilibrium exists between the two H-bonding isomers DHDA-23-OO and DHDA-23-OI, both of which possess double intramolecular H-bonds. In polar, aprotic solvents such as CH2Cl2, DHDA-23-OO becomes the predominant species. Due to various degrees of H-bond induced changes of electronic configuration each isomer reveals a distinct absorption feature and excited-state behavior, in which DHDA-23-OI in cyclohexane undergoes double ESIPT in a stepwise manner, giving the first and second proton-transfer tautomer emissions maximized at ～500 nm and 660 nm, respectively. As for DHDA-23-OO both single and double ESIPT are prohibited, resulting in an intense normal 450 nm emission band. In a single crystal DHDA-23-OI is the dominant species, which undergoes excited state double proton transfer, giving intense emission bands at 530 nm and 650 nm. The mechanism associated with competitive multiple H-bonding energetics and ESIPT was underpinned by detailed spectroscopy/dynamics and computational approaches.

Bimetallic effects for enhanced polar comonomer enchainment selectivity in catalytic ethylene polymerization

The synthesis and characterization of the bimetallic 2,7-di-[(2,6- diisopropylphenyl)imino]-1,8- naphthalenediolato group 10 metal polymerization catalysts {[Ni(CH 3)] 2[1,8-(O) 2C 10H 4-2,7-[CH=N(2,6- Pr 2C 6H 3)](PMe 3) 2} and {[Ni(1-naphthyl)] 2[1,8-(O) 2C 10H 4-2,7-[CH=N(2,6-Pr 2C 6H 3)](PPh 3) 2} [FI 2-Ni 2(PR 3) 2] are presented, along with the synthesis and characterization of the mononuclear analogues {Ni(CH 3)[3- tBu- 2-(0)C 6H 3CH=N(2,6- iPr 2C 6H 3)](PMe) 3}and{Ni(1-naphthyl)[3- tBu-2-(0)C 6H 3CH=N(2,6- iPr 2C 6H 3)](PPh) 3}[FI- Ni (PR 3)].Monometallic Ni catalysts were also prepared by functionalizing one lig ation center of the bimetallic ligand with a trimethylsilyl group (TMS),yielding {Ni(CH 3)[1,8-(O)(TMSO)C 10H 4-2,7-[CH=N(2,6- iPr 2C 6H 3)](PMe 3)} [TMS-FI 2-Ni(PMe 3)]. The Fl2-Ni 2 catalysts exhibit significant increases in ethylene homopolymerization activity versus the monometallic analogues, as well as increased branching and methyl branch selectivity, even in t he absence of a Ni(cod) 2 cocatalyst. Increasing ethylene concentrations significantly suppress branching and alter branch morphology. FI 2-Ni 2-mediated copolymerizations with ethylene + polar-functionalized norbornenes exhibit a 4-fold increase in comonomer incorporation versus Fl-Ni, yielding copolymers with up to 10percent norbornene copolymer incorporation. FI 2-Ni 2-catalyzed copolymerizations with ethylene + methylacrylate or methyl methacrylate incorporate up to 11percent acrylate comonomer, while the corresponding mononuclear Fl-Ni catalysts incorporate negligible amounts. Furthermore, the FI 2-Ni 2-mediated polymerizations exhibit appreciable polar solvent tolerance, turning over in the presence of ethyl ether, acetone, and even water. The mechanism by which the present cooperative effects take place is investigated, as is the nature of the copolymer microstructures produced.

A streamlined synthesis for 2,7-diformyl-1,8-naphthalenediol

2,7-Diformyl-1,8-naphthalenediol, an extension of the numerously used precursor 2,6-diformylphenol for the synthesis of various ligand systems, has been synthesized by a double Directed ortho Metalation reaction.