Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-11-20
2003-10-07
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C540S132000, C544S223000, C568S038000, C568S039000, C568S041000, C568S061000, C549S227000
Reexamination Certificate
active
06630578
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel thioether derivatives, the production method and use thereof, and relates especially to the S containing dendrimers and the synthetic intermediates thereof.
2. Description of the Prior Art
The dendritic molecules, having a unique macromolecular structure, are expected to have a wide field of application. The dendritic molecules which have a unique chemical structure composed of a central core (nucleus), and a branch structure constructed with branches (units) repeated regularly and the surface functional groups, both extending three-dimensionally, have been investigated actively in the field, for example, of nano science, communication science, electro-material science, medical science, pharmaceutical science, biological science, surface science and material science, and so on (References: “Dendritic Molecules”, VCH Publication Co. 1996; “Molecular Design of Dendrimers” and “Miscellaneous Functions of Dendrimers” Gendai Kagaku, June, 1998, on pp. 20-40; “Applications of Dendrimers as Non-linear Optical Materials” in Kobunshi, Vol.47, November, 1998.) It may safely be said, however, that the dendrimer science is “one of the latest sciences”, because it has been highlighted only since about the middle of the year 1990 and the number of the research on it has increased recently.
As for the use of the dendritic molecules, there have been offered a variety of inventions on the subject of industrial use thereof, for example, their use in medicine and agricultural chemicals (JP-A Hei7-330631), use in solar cell and photosensitive material for electrophotography (JP-A Hei11-40871), use in electronic material (JP-A Hei11-171812), use in liquid crystal (JP-A 2000-264965), use in paint and ink (JP-A Hei11-140180), use in fluorescent resin sheet (JP-A Hei11-323324), use in qualitative and quantitative analyses (JP-A Hei11-218494), use in biological response modifier (JP-C Hei8-510761), and so on.
SUMMARY OF THE INVENTION
The object of the present invention is to provide both novel dendritic molecules with useful functions and novel synthetic intermediates for producing them.
More specifically, the main object of the present invention is to provide novel dendrimers which are useful as electronic material (for example, as the switch of memory) due to their ability to emit light from the core by transferring electron which exists in the branch structure into the core which has been made electron deficient by absorbing light or electric energy.
Other objects of the present invention will become clear through the explanation hereinafter.
The present inventors made an intensive investigation on the aforementioned problems and succeeded in creating the S atom containing dendrimers of the present invention.
In addition, the present inventors have obtained a lot of novel knowledge about the dendrimers of the present invention which have many sulfur atom in their branch structures. Namely, in the case of the sulfur atom we can make use of their d-orbital electrons which do not exist in the oxygen atom. As the d-orbital electrons of the sulfur atom are placed farther apart from the nuclei than the p-orbital electrons of the oxygen atom, the electrons of the sulfur atom can move more freely than the electrons of the oxygen atom; the light or electric energy can be transferred to the core, which is in an electron-deficient state, with ease; it becomes possible to make the core emit light by constructing the core from a residue of a luminescent compound; and a larger polarization between the branch structure and the core can be obtained with the sulfur atoms than with the oxygen atoms. Consequently, the present inventors have got the knowledge that the dendrimers of the present invention are useful as an electronic material, for example, as the switch of memory.
In addition, the present inventors have found that, although S atom-containing dendrimers can suffer deterioration due to oxidation, it is possible to make them more durable and of a long life by placing substituents with steric bulkiness, preferably t-butyl groups, on the outside of the branch structure, namely, at the opposite end across the branch structure from the core.
Furthermore, the present inventors have found that the S atom-containing dendrimers of the present invention can be produced conveniently and industrially advantageously from a series of novel synthetic intermediates of specific structures.
Based on a lot of novel knowledge mentioned above, the present inventors have carried out an intensive investigation on the subject and completed the present invention.
That is to say, the present invention relates to the compounds and salts thereof:
[1] A dendritic molecule characterized in that it comprises or preferably has a core, a branch structure composed of Unit 1 represented by the following structure,
, wherein ring A stands for a homo- or heterocyclic six-membered ring, and surface functional groups as the essential constituents.
[2] A dendritic molecule characterized in that it comprises or preferably has a core, a branch structure composed of both Unit 1 described in [1] and Unit 2 represented by the following structure,
, wherein ring A stands for a homo- or heterocyclic six-membered ring, and/or Unit 3 represented by the following structure,
, wherein ring A stands for a homo- or heterocyclic six-membered ring, and the surface functional groups.
[3] A dendritic molecule characterized in that it comprises or preferably has a core, a branch structure composed of two or more of the partial branch structures of Unit 1 described in [1], Unit 2 described in [2], and Unit 3 in [2], and the surface functional groups.
[4] A dendritic molecule of any of [1] and [2], wherein the branch structure is of 2-10 generations and is constructed with both a generation or generations of the branch structure composed of Unit 1 described in [1] and a generation or generations of the branch structure Unit 2 described in [2] and/or Unit 3 described in [2].
[5] A dendritic molecule of [1] to [4], wherein the ring A of Unit 1, Unit 2 and Unit 3 is a benzene ring, a pyrimidine ring or a triazine ring.
[6] A dendritic molecule of [1] to [5], wherein the surface functional group is an alkyl group which may be substituted, an aralkyl group which may be substituted, an alkoxy group, an alkoxycarbonyl group or a quaternary ammonium group.
[7] A dendritic molecule of [6], wherein the surface functional group is a t-butyl group.
[8] A dendritic molecule of [1] to [7], wherein the core is a color developing functional group.
[9] A dendritic molecule of [1] to [7], wherein the core is a rhodamine pigment, a quinazoline, a perylene, an azo-compound, 2,5-dihydroxybenzoic acid methyl ester, a porphyrin, 4,4′-dihydroxybiphenyl or 1-(4.4′,4″-trihydroxyphenyl)ethane residue.
[10] A thio-compound represented by the following structure,
wherein ring A is a ring represented by Formula 5,
which has each of the substituent B, substituent C and substituent D at the positions denoted with a bond, and may be substituted at the positions where no bond is attached;
substituent B stands for —S(O)nR
1
,
wherein n stands for an integer of 0-2, and R
1
stands for a substituent;
substituent C stands for —X
1
R
2
,
wherein X
1
stands for a intervening group, and R
2
stands for a substituent; and
substituent D stands for a substituent bonded to the ring A through a carbon atom.
[11] A thio-compound of [10], wherein R
1
and R
2
are, each being the same or different, an alkali metal, a hydrogen atom, an alkyl group which may be substituted, an aralkyl group, a carbamoyl group or a thiocarbamoyl group.
[12] A thio-compound of [10] or [11], w
Mashiko Shinro
Miki Hideki
Nakahama Tatsuo
Yokoyama Shiyoshi
Barts Samuel
Communications Research Laboratory, Independent Administrative I
Zucker Paul A.
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