JPH04120085A - Porphyrin derivative - Google Patents
Porphyrin derivativeInfo
- Publication number
- JPH04120085A JPH04120085A JP23938490A JP23938490A JPH04120085A JP H04120085 A JPH04120085 A JP H04120085A JP 23938490 A JP23938490 A JP 23938490A JP 23938490 A JP23938490 A JP 23938490A JP H04120085 A JPH04120085 A JP H04120085A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- porphyrin derivative
- substituted
- materials
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000004033 porphyrin derivatives Chemical class 0.000 title claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 7
- 230000003287 optical effect Effects 0.000 abstract description 5
- -1 (substituted) phenyl Chemical group 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- 230000015654 memory Effects 0.000 abstract description 3
- 239000011941 photocatalyst Substances 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KAQQQJHJILHTCD-UHFFFAOYSA-N acetonitrile;chloroform;methanol Chemical compound OC.CC#N.ClC(Cl)Cl KAQQQJHJILHTCD-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野１
本発明は新規なポルフィリン誘導体に関するものである
。詳しくは光電運用材料、電子写真感光体用材料、光メ
モリー用材料、光触媒用材料、分子素子用材料等として
使用し得る新規なポルフィノン系化合物に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application 1] The present invention relates to a novel porphyrin derivative. Specifically, the present invention relates to novel porphynone compounds that can be used as photoelectric operating materials, electrophotographic photoreceptor materials, optical memory materials, photocatalytic materials, molecular device materials, and the like.
［従来の技術および発明が解決しようとする課題１ポル
フイリンは平面４座配位子の一つで、周期律表ＩＡ〜７
Ａ、８、ＩＢ〜５Ｂ族の各金属元素と錯体を形成するこ
とが知られている。そしてこれらのポルフィリン誘導体
の中には、ヘモグロビン、ジアノコバラミン、クロロフ
ィル等のように生体機能と関連するものが数多く知られ
ているが、一方でその光学的な特性を生かして、情報・
電子材料の分野においてもにわかに注目を集めている。[Problems to be solved by the prior art and the invention 1 Porphyrin is one of the planar tetradentate ligands, and is classified into IA to 7 of the periodic table.
It is known to form complexes with metal elements of groups A, 8, IB to 5B. Among these porphyrin derivatives, many are known to be related to biological functions, such as hemoglobin, dianocobalamin, and chlorophyll, but on the other hand, by taking advantage of their optical properties, information and
It is also suddenly attracting attention in the field of electronic materials.
［課題を解決するための手段１
本発明者らは、ポルフィリン誘導体の光学特性に着目し
、新たな機能材料を提供するべく検討を重ねた結果、ポ
ルフィリン骨格の中心部にリンが配位した化合物がかか
る機能を有することを見出し、本発明を完成するに至っ
た。[Means for Solving the Problems 1 The present inventors focused on the optical properties of porphyrin derivatives and, as a result of repeated studies to provide new functional materials, developed a compound in which phosphorus is coordinated at the center of the porphyrin skeleton. The present inventors have discovered that the present invention has such a function, and have completed the present invention.
即ち、本発明は、一般式［Ｉ］
ＯＲ’
（式中、Ｒ１は、ヒドロキシル基もしくはフェニル基で
置換されていてもよいアルキル基、シクロアルキル基、
置換基を有していてもよいフェニル基またはアシル基を
示し、Ｒ２は置換基を有していてもよいフェニル基を示
す。Ｘｅは１価の陰イオンを示す。）で表わされるポル
フィリン誘導体を要旨とするものである。That is, the present invention relates to the general formula [I] OR' (wherein R1 is an alkyl group, a cycloalkyl group, which may be substituted with a hydroxyl group or a phenyl group,
It represents a phenyl group or an acyl group which may have a substituent, and R2 represents a phenyl group which may have a substituent. Xe represents a monovalent anion. ) This article focuses on porphyrin derivatives represented by:
以下、本発明につき、詳細に説明する。Hereinafter, the present invention will be explained in detail.
本発明のポルフィリン誘導体は、前記一般式［ＩＩで表
わされ、Ｒ１としては炭素数１〜３０のアルキル基が挙
げられ、これはヒドロキシル基またはフェニル基で置換
されていてもよい。The porphyrin derivative of the present invention is represented by the general formula [II, where R1 is an alkyl group having 1 to 30 carbon atoms, which may be substituted with a hydroxyl group or a phenyl group.
また、Ｒ１としてはシクロヘキシル基等のシクロアルキ
ル基、置換基（例えば、炭素数１〜３０のアルキル基、
炭素数１〜３０のアルコキシ基、クロル原子、ブロム原
子、フッ素原子、ヨード原子等のハロゲン原子またはニ
トロ基等があげられる。）を有していてもよいフェニル
基もしくはアシル基［Ｒ３Ｃ０−（例えば、Ｒ３は炭素
数１〜３０のアルキル基；トリフルオロメチル基、ジク
ロルメチル基等のハロゲン原子で置換されたアルキル基
；Ｒ１と同じ置換基を有していてもよいフェニル基が挙
げられる。）〕が挙げられる。Ｒ２としてはＲ１と同じ
置換基を有していてもよいフェニル基が挙げられる。尚
、Ｒ’ −Ｒ３で挙げたアルキル基またはアルコキシ基
としては直鎖または分岐鎖状のいずれでもよい。Ｘｅで
示される１価の陰イオンとしてはクロルイオン、ブロム
イオン、ヨードイオン等のハロゲンイオンや硝酸イオン
、酢酸イオン等が挙げられる。Further, as R1, a cycloalkyl group such as a cyclohexyl group, a substituent (for example, an alkyl group having 1 to 30 carbon atoms,
Examples include an alkoxy group having 1 to 30 carbon atoms, a halogen atom such as a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, or a nitro group. ) may have a phenyl group or an acyl group [R3C0- (for example, R3 is an alkyl group having 1 to 30 carbon atoms; an alkyl group substituted with a halogen atom such as a trifluoromethyl group or a dichloromethyl group; R1 and Examples include phenyl groups which may have the same substituents.)]. Examples of R2 include phenyl groups which may have the same substituents as R1. Incidentally, the alkyl group or alkoxy group mentioned for R'-R3 may be either linear or branched. Examples of the monovalent anion represented by Xe include halogen ions such as chlorine ion, bromide ion, and iodo ion, nitrate ion, and acetate ion.
本発明の一般式［ＩＩのポルフィリン誘導体は以下の様
にして製造することが出来る。The porphyrin derivative of the general formula [II of the present invention can be produced as follows.
［１１１
［■月
［１］
すなわち、本発明の一般式［ＩＩのポルフィリン誘導体
は一般式［ＩＩ ］で示されるポルフィリン誘導体に一
般式［ＩＩＩ］を反応させることにより得ることが出来
る。[111 [■ Month [1] That is, the porphyrin derivative of the general formula [II] of the present invention can be obtained by reacting the porphyrin derivative represented by the general formula [II] with the general formula [III].
本反応は例えば２０’Ｃ〜１２０’Ｃで数時間加熱する
ことにより達成される。本反応においては、アセトニト
リル等の溶媒を使用してもよい。This reaction is accomplished, for example, by heating at 20'C to 120'C for several hours. In this reaction, a solvent such as acetonitrile may be used.
また、Ｒ１がアルキル基の場合、本反応、はキセノンラ
ンプ等を使用した光反応により脱酸素下、より短時間（
〜数分間）で完了することが出来る。In addition, when R1 is an alkyl group, this reaction can be carried out in a shorter time (
It can be completed in a few minutes).
原料として使用する一般式［ＩＩ ］の化合物は、一般
式［ＩＶ］
で表わされるポルフィリン誘導体に、例えばＰＯＣｌ３
を反応させることにより得ることが出来る。The compound of general formula [II] used as a raw material is a porphyrin derivative represented by general formula [IV], for example, POCl3
It can be obtained by reacting.
［発明の効果］
本発明ポルフィリン誘導体は、光電専用材料、電子写真
感光体用材料、光メモリー用材料、光触媒用材料、分子
素子用材料等として有用である。[Effects of the Invention] The porphyrin derivatives of the present invention are useful as materials for photoelectric use, materials for electrophotographic photoreceptors, materials for optical memories, materials for photocatalysts, materials for molecular devices, and the like.
［実施例］
次に本発明を実施例により更に具体的に説明するが、本
発明は以下の実施例により限定されるものではない。[Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples.
実施例１
下記一般式［ＩＡ］で示される化合物の合成例メタノー
ル１５ｍ１に溶解し、７時間加熱還流する。Example 1 Synthesis example of a compound represented by the following general formula [IA] Dissolved in 15 ml of methanol and heated under reflux for 7 hours.
反応液を濃縮後、アルミナ（ｎｅｕｔｒａｌ、■）を担
体とし、クロロホルム−メタノール（１０：１）を分離
溶媒とするカラムクロマトグラフィーで精製して目的の
ポルフィリン誘導体を９９ｍｇ得た。After concentrating the reaction solution, it was purified by column chromatography using alumina (neutral, ■) as a carrier and chloroform-methanol (10:1) as a separation solvent to obtain 99 mg of the desired porphyrin derivative.
得られた前記一般式［ＩＡ］で示される化合物の分析結
果は以下の通りである。The analysis results of the obtained compound represented by the general formula [IA] are as follows.
・ ＩＨ−ＮＭＲ（ＣＤＣｌ３、ＴＭＳ）δ９．０７
（ｄ ）、７．９５（ｍ ）
７．７８ （ｍ ）
−１，８７（ｄ、 ６Ｈ）
・ ３１Ｐ−ＮＭＲ（ＣＤＣｌ３、外部基準８０％Ｈ３
ＰＯ４ｔｎ Ｄ２０ ）δ−１７８，１
・ ＵＶ−ＶＩＳ （ＣＨＣｌ３ ）λｍａｘ （ｎｍ
） ４３０．５６０．６０２・ Ｅｍｉｓｓｉｏｎ
ｓｐｅｃｔｒｕｍ （ＣＨＣｌ３ ）λｍａｘ ｎｍ
６１５，６７０・ ＩＲ（ＫＢｒ、ｃｍ−’） １
０５７＠ Ｅ” （１）（ＶｖｓＳＣＥ）−０，５０
［実施例２〜９］
実施例１と同様にして、前記の一般式［Ｉ］において、
Ｒ２がフェニル基でＸｅがＯｌｅであり、Ｒ１が下言己
の第１表に示される基であるポルフィリン誘導体を製造
した。・IH-NMR (CDCl3, TMS) δ9.07
(d), 7.95 (m) 7.78 (m) -1,87 (d, 6H) 31P-NMR (CDCl3, external standard 80% H3
PO4tn D20 ) δ-178,1 ・UV-VIS (CHCl3 ) λmax (nm
) 430.560.602・ Emission
spectrum (CHCl3)λmax nm
615,670・IR (KBr, cm-') 1
057@E” (1) (VvsSCE) -0,50
[Examples 2 to 9] In the same manner as in Example 1, in the general formula [I],
Porphyrin derivatives were prepared in which R2 is a phenyl group, Xe is Ole, and R1 is a group shown in Table 1 below.
以下の第１表にＩＨ−ＮＭＲ１３１Ｐ −ＮＭＲｌＩＲ
の分析結果を示す。IH-NMR131P-NMRlIR is shown in Table 1 below.
The analysis results are shown below.
実施例１０
１００°Ｃで６時間加熱した。フェノールを減圧留去し
た後、実施例１と同様のカラムクロマトグラフィーによ
り精製し、その後、更に、シリカゲルを担体とし、クロ
ロホルム−アセトニトリル−メタノール（２０：９：１
）を分離溶媒とするカラムクロマトグラフィーにより精
製して目的のポルフィリン誘導体を得た。（収率７１％
）。Example 10 Heated at 100°C for 6 hours. After distilling off the phenol under reduced pressure, it was purified by the same column chromatography as in Example 1. Then, using silica gel as a carrier, chloroform-acetonitrile-methanol (20:9:1
) was purified by column chromatography using as a separation solvent to obtain the desired porphyrin derivative. (yield 71%
).
得られたポルフィリン誘導体の分析結果は以下の通りで
ある。The analysis results of the obtained porphyrin derivative are as follows.
ＩＨＮＭＲ（ＣＤＣ１３、ＴＭＳ）
６９．０３ （ｄ、 ８Ｈ，Ｊｐ、Ｈ＝ ３．５ Ｈ２
）７．７６ （ｓ、 ｂｒ、 ２０ Ｈ）６．０１ （
ｍ、 ６Ｈ）
２．２１ （ｄ、 ４Ｈ）
３１ＰＮＭＲ（ＣＤＣｌ３、外部基準８０％Ｈ３ＰＯ４
ｉｎ Ｄ２０ ）δ −１９４，７
ＵＶ −ＶＩＳ （ＣＨＣｌ３）λｍａｘ、 ｎｍ ４
３６．５６２．６０４Ｅｍｉｓｓｉｏｎ ｓｐｅｃｔｒ
ｕｍ （ＣＤＣｌ３ ） λｍａｘ、ｎｍ ６２０，
６７３ＩＲ（ＫＢｒ、 ａｍ’ ） ８８６ｅｄ
Ｅ （１）（ＶｖｓＳＣＥ）−０，３９１／２
実施例１１
実施例１０と同様にして、
合成した。その分析結果を以下に示す。IHNMR (CDC13, TMS) 69.03 (d, 8H, Jp, H = 3.5 H2
)7.76 (s, br, 20 H)6.01 (
m, 6H) 2.21 (d, 4H) 31PNMR (CDCl3, external reference 80% H3PO4
in D20) δ -194,7 UV-VIS (CHCl3) λmax, nm 4
36.562.604Emission spectrum
um (CDCl3) λmax, nm 620,
673IR (KBr, am') 886ed E (1) (VvsSCE)-0,391/2 Example 11 Synthesized in the same manner as Example 10. The analysis results are shown below.
’ＨＮＭＲ（ＣＤＣ１３、ＴＭＳ）
δ９．１２ ７．７０ （Ｓ、 ｂｒ、 ２０Ｈ）６．
８８（ｄ、４Ｈ） ２．４１（ｄ、４Ｈ）３１ＰＮＭ
Ｒ（ＣＤＣ１３、
−１９９，３
外部基準８０％Ｈ３ＰＯ４ｉｎ Ｄ２０ ）ＵＶ Ｖ
ＩＳ （ＣＨ３ＣＮ ）λｍａｘＥ”ｄ （１）（Ｖ
ｖｓＳＣＥ）−０，２９４３３、５６１，６０２
実施例１２
撹拌した。酢酸を減圧、留去後、実施例１と同様なカラ
ムクロマトグラフィーにより、目的のポルフィリン誘導
体を得た。（収率７０％）。'HNMR (CDC13, TMS) δ9.12 7.70 (S, br, 20H)6.
88 (d, 4H) 2.41 (d, 4H) 31PNM
R (CDC13, -199,3 External standard 80% H3PO4in D20) UV V
IS (CH3CN)λmaxE”d (1)(V
vsSCE)-0,29433,561,602 Example 12 Stirred. After acetic acid was distilled off under reduced pressure, the desired porphyrin derivative was obtained by column chromatography in the same manner as in Example 1. (Yield 70%).
得られたポルフィリン誘導体の分析結果は以下の通りで
ある。The analysis results of the obtained porphyrin derivative are as follows.
’ＨＮＭＲ（ＣＤＣ１３、ＴＭＳ）
８９．０３ （ｄ、 ＪＰ、Ｈ＝ ４．０Ｈｚ ）７．
９０（ｍ） ７．７８（ｍ）
−０，６１（ｄ、 ６Ｈ，ＪＰ、Ｈ＝ ３．１Ｈｚ ）
”Ｐ ＮＭＲ（ＣＤＣ１ａ、外部基準８０％Ｈ３Ｐ０４
ｔｎ Ｄ２０ ）δ −２１０，３
ＵＶ −ＶＩＳ （ＣＨＣｌ３ ） λｍａｘ、 ｎ
ｍ ４３４．５６４．６０７Ｅｍｉｓｓｉｏｎ ｓｐ
ｅｃｔｒｕｍ （ＣＨＣｌ３ ） λｍａｘ、 ｎｍ
６２０．６７５ＩＲ（ＫＢｒ、ａｍ’） ９１
０
Ｅ （１）（ＶｖｓＳＣＥ） −０，３７実施例１３
〜１５
実施例１２と同様にして前言己一般式［Ｉ］において、
Ｒ２＝Ｐｈ （７ｘ ニール基）、Ｘｅ＝Ｃ１ｅであり
、Ｒ＋が下記第２表に示される基であるポルフィリン誘
導体をそれぞれ製造した。'HNMR (CDC13, TMS) 89.03 (d, JP, H=4.0Hz)7.
90 (m) 7.78 (m) -0,61 (d, 6H, JP, H = 3.1Hz)
”P NMR (CDC1a, external standard 80% H3P04
tn D20 ) δ -210,3 UV-VIS (CHCl3) λmax, n
m 434.564.607Emission sp
ectrum (CHCl3) λmax, nm
620.675IR (KBr, am') 91
0 E (1) (VvsSCE) -0,37 Example 13
~15 In the same manner as in Example 12, in the general formula [I],
Porphyrin derivatives were prepared in which R2=Ph (7x Neil group), Xe=C1e, and R+ was a group shown in Table 2 below.
以下の第２表に、ＩＨ−ＮＭＲ１３１Ｐ −ＮＭＲｌＩ
Ｒの分析結果を示す。Table 2 below shows IH-NMR131P-NMRlI
The analysis results of R are shown.
Claims (1)
で置換されていてもよいアルキル基、シクロアルキル基
、置換基を有していてもよいフェニル基またはアシル基
を示し、Ｒ＾２は置換基を有していてもよいフェニル基
を示す。Ｘ＾■は１価の陰イオンを示す。）で表わされ
るポルフィリン誘導体。(1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, R^1 is an alkyl group, cycloalkyl, which may be substituted with a hydroxyl group or a phenyl group. (R^2 represents a phenyl group that may have a substituent. X^■ represents a monovalent anion.) A porphyrin derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23938490A JP2917471B2 (en) | 1990-09-10 | 1990-09-10 | Porphyrin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23938490A JP2917471B2 (en) | 1990-09-10 | 1990-09-10 | Porphyrin derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04120085A true JPH04120085A (en) | 1992-04-21 |
| JP2917471B2 JP2917471B2 (en) | 1999-07-12 |
Family
ID=17043986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23938490A Expired - Lifetime JP2917471B2 (en) | 1990-09-10 | 1990-09-10 | Porphyrin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2917471B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010209044A (en) * | 2009-03-12 | 2010-09-24 | Toyota Motor Corp | Dinuclear metal complex and photocatalyst containing the same |
| US8846904B2 (en) | 2009-10-07 | 2014-09-30 | University Of Miyazaki | Water-soluble porphyrin and process for production thereof |
| WO2015170562A1 (en) * | 2014-05-08 | 2015-11-12 | 国立大学法人静岡大学 | Phosphorus porphyrin compound, method for producing same, and biomolecule damaging agent |
-
1990
- 1990-09-10 JP JP23938490A patent/JP2917471B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010209044A (en) * | 2009-03-12 | 2010-09-24 | Toyota Motor Corp | Dinuclear metal complex and photocatalyst containing the same |
| US8846904B2 (en) | 2009-10-07 | 2014-09-30 | University Of Miyazaki | Water-soluble porphyrin and process for production thereof |
| WO2015170562A1 (en) * | 2014-05-08 | 2015-11-12 | 国立大学法人静岡大学 | Phosphorus porphyrin compound, method for producing same, and biomolecule damaging agent |
| JPWO2015170562A1 (en) * | 2014-05-08 | 2017-04-20 | 国立大学法人静岡大学 | Limporphyrin compound, production method thereof, and biomolecule damaging agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2917471B2 (en) | 1999-07-12 |
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