The fluorine-containing ether compound is represented by the following formula (1): R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4. In the formula (1), R.sup.1 is represented by the following formula (2), R.sup.2 is represented by the following formula (3), R.sup.3 is a perfluoropolyether chain, and R.sup.4 is an organic end group different from R.sup.1—R.sup.2— and contains two or three polar groups, wherein each polar group is bonded to a different carbon atom, and the carbon atoms to which the polar groups are bonded are bonded to one another via a linking group containing a carbon atom to which the polar group is not bonded. In the formula (2), r is 1 to 3. In the formula (3), w is 2 or 3. ##STR00001##

To improve the emission efficiency, the driving voltage and the lifetime of an organic light-emitting device using a delayed fluorescent material. A host material for a delayed fluorescent material, containing a compound represented by the following general formula: R.sup.1 to R.sup.5 each are a substituent not containing a cyano group. n1 to n5 each are 0 to 4, Ar is a monocyclic arylene group or a monocyclic heteroarylene group.

##STR00001##

The present invention relates to guanidine compounds for inhibiting mitochondrial oxidative phosphorylation (OXPHOS) and use thereof. More specifically, the present invention relates to a pharmaceutical composition for preventing or treating a OXPHOS-related disease, particularly cancer, by inhibiting mitochondrial oxidative phosphorylation and reprogramming cellular metabolism.

The present invention relates to guanidine compounds for inhibiting mitochondrial oxidative phosphorylation (OXPHOS) and use thereof. More specifically, the present invention relates to a pharmaceutical composition for preventing or treating a OXPHOS-related disease, particularly cancer, by inhibiting mitochondrial oxidative phosphorylation and reprogramming cellular metabolism.

The invention provides surfactant compounds of formulas I-IX, which can be used in methods for aiding the solubilization, digestion, preparation, analysis, and/or characterization of biological material, for example, proteins or cell membranes. The compounds can also aid in the recovery of peptides generated during protein digestion, particularly for in-gel digestion protocol. Additionally, the compounds can improve enzymatic protein deglycosylation without interfering with downstream sample preparation steps and mass spectrometric analysis. The compounds can be specifically useful as digestion aids that can be decomposed by an acid, by heat, or a combination thereof. Decomposition of the surfactants allows for facile separation from isolated samples, and/or allows for analysis of the sample without interfering with the sensitivity of various analytical techniques.

The invention provides surfactant compounds of formulas I-IX, which can be used in methods for aiding the solubilization, digestion, preparation, analysis, and/or characterization of biological material, for example, proteins or cell membranes. The compounds can also aid in the recovery of peptides generated during protein digestion, particularly for in-gel digestion protocol. Additionally, the compounds can improve enzymatic protein deglycosylation without interfering with downstream sample preparation steps and mass spectrometric analysis. The compounds can be specifically useful as digestion aids that can be decomposed by an acid, by heat, or a combination thereof. Decomposition of the surfactants allows for facile separation from isolated samples, and/or allows for analysis of the sample without interfering with the sensitivity of various analytical techniques.

Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.

Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.

An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1):

##STR00001##

wherein
R.sup.a1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents,
Rf is a fluoro group or a perfluoroalkyl group,
R.sup.a2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or
(i) R.sup.a1 and R.sup.a2, (ii) R.sup.a1 and Rf, or (iii) Rf and R.sup.a2 may be linked to each other,
R.sup.b1 is R.sup.s,
R.sup.b2 is a hydrogen atom or R.sup.s,
R.sup.b3 is a hydrogen atom or R.sup.s, or
two or three of R.sup.b1, R.sup.b2, and R.sup.b3, taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and
R.sup.s, in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising
step A of reacting a compound represented by formula (2):

##STR00002##

wherein
R.sup.x is a leaving group, and
other symbols are as defined above,
with a compound represented by formula (3):

##STR00003##

wherein the symbols in the formula are as defined above,
in the presence of a transition metal catalyst.

Provided is a fluorine-containing ether compound that can be suitably used as a material for a lubricant for a magnetic recording medium, capable of forming a lubricant layer having excellent chemical substance resistance and wear resistance even when the thickness is small. A fluorine-containing ether compound represented by the following formula (1):
R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) In the formula (1), R.sup.3 is a perfluoropolyether chain. R.sup.2 and R.sup.4 are divalent linkage groups having a polar group, and may be the same or different. R.sup.1 and R.sup.5 are terminal groups bonded to R.sup.2 or R.sup.4, which may be the same or different, and at least one of R.sup.1 and R.sup.5 is an organic group having 1 to 8 carbon atoms wherein one or more hydrogen atoms of the organic group is substituted with a cyano group.