# US 5,710,273 A · Complex crystal comprising tricyclic organic bases > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,710,273 A - Document ID: US5710273A - Status: Granted - Kind: A - Application number: 08/686,040 - Filed: 1996-07-25 - Granted: 1998-01-20 - Earliest claimed: 1991-12-12 - Assignees: Toyota Jidosha Kabushiki Kaisha; Kabushiki Kaisha Toyota Chuo Kenkyusho - Inventors: Arimitsu Usuki; Hisato Takeuchi; Narihito Tatsuda; Akane Okada; Toshio Kurauchi; Hiromitsu Tanaka; Shinobu Okayama; Kazuo Tojima; Akio Fukui; Toshiro Okamoto - Web page: https://patentgrep.com/patent/US5710273A ## CPC - C07D 471/04: Ortho-condensed systems - C07D 219/02: with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system - C07D 221/12: Phenanthridines - G02F 1/0009: {Materials therefor} - G02F 1/172: {based on a suspension of orientable dipolar particles, e.g. suspended particles displays} - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS ## Abstract A complex crystal is composed of anion of triiodine and cation of a fused compound consisting essentially of at least one nitrogen atom and at least 3 aromatic fused rings. Since the complex crystal has such a stable structure, it shows excellent heat resistance and excellent moisture resisting property. Furthermore, the complex crystal has light-polarizing performance because of an arrangement of the molecular chain of iodine. Moreover, the complex crystal exhibits excellent polarization because of an interaction between the fused compound and iodine. Therefore, the complex crystal is suitable for use as light-adjusting particles of a light valve or a light-adjusting glass. ## Claims ### Claim 1 A complex crystal consisting essentially of: the anion of triiodine; the cation of acridine or a derivative thereof having a basic property; and the anion of a Bronsted acid selected from the group consisting of sulfuric, hydrochloric, phosphoric, hydroiodic, sulfonic, monocarboxylic, and dicarboxylic acids, wherein the cation and the Bronsted acid anion form a neutral salt, so that an electron placed on the complex crystal is likely to move because of an interaction between the salt and the triiodine anion. ### Claim 2 A complex crystal consisting essentially of; the anion of triiodine; the cation of pyrazino (2,3-f) phenanthroline, dipyrido (3,2-a; 2',3'-c) phenazine, or a derivative thereof having a basic property; and the anion of a Bronsted acid selected from the group consisting of sulfuric, hydrochloric, phosphoric, hydroiodic, sulfonic, monocarboxylic, and dicarboxylic acids, wherein the cation and the Bronsted acid anion form a neutral salt, so that an electron placed on the complex crystal is likely to move because of an interaction between the salt and the triiodine anion. ### Claim 3 (depends on 1) A complex crystal according to claim 1, wherein the Bronsted acid is sulfuric acid. ### Claim 4 (depends on 2) A complex crystal according to claim 2, wherein the Bronsted acid is sulfuric acid. ### Claim 5 (depends on 1) A complex crystal according to claim 1, wherein the Bronsted acid is at least one selected from the group consisting of trifluoroacetic acid, oxalic acid, malonic acid, succinic acid, L-tartaric acid, dibenzoyl-L-tartaric acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid. ### Claim 6 (depends on 2) A complex crystal according to claim 2, wherein the Bronsted acid is at least one selected from the group consisting of trifluoroacetic acid, oxalic acid, malonic acid, succinic acid, L-tartaric acid, dibenzoyl-L-tartic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid. ### Claim 7 (depends on 1) A complex crystal according to claim 1, wherein the Bronsted acid is at least one selected from the group consisting of hydrochloric acid, phosphoric acid, hydroiodic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, acetic acid, propionic acid, butyric acid, valeric acid, benzoic acid, malonic acid and phthalic acid. ### Claim 8 (depends on 2) A complex crystal according to claim 2, wherein the Bronsted acid is at least one selected from the group consisting of hydrochloric acid, phosphoric acid, hydroiodic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, acetic acid, propionic acid, butyric acid, valeric acid, benzoic acid, malonic acid and phthalic acid. ### Claim 9 (depends on 1) A complex crystal according to claim 1, wherein the melting point of the complex crystal is in the vicinity of 205.degree. C. ### Claim 10 (depends on 2) A complex crystal according to claim 2, wherein the melting point of the complex crystal including the pyrazino (2,3-f) phenanthroline is in the vicinity of 288.degree. C. ### Claim 11 (depends on 2) A complex crystal according to claim 2, wherein the melting point of the complex crystal including the dipyrido (3,2-a; 2',3'-c) phenazine is in the vicinity of 297.degree. C. ### Claim 12 (depends on 1) A complex crystal according to claim 1, wherein the color of the complex crystal shows no change when the dispersed liquid of the complex crystal is heated at a temperature of 130.degree. C. for 10 hours. ### Claim 13 (depends on 2) A complex crystal according to claim 2, wherein the color of the complex crystal shows no change when the dispersed liquid of the complex is heated at a temperature of 130.degree. C. for 10 hours. ### Claim 14 (depends on 1) A complex crystal according to claim 1, wherein the color of the complex crystal shows no change when the complex crystal is mixed with water. ### Claim 15 (depends on 2) A complex crystal according to claim 2, wherein the color of the complex crystal shows no change when the complex crystal is mixed with water. ### Claim 16 (depends on 3) A complex crystal according to claim 3, wherein the molar ratio of the acridine, the triiodine and the sulfuric acid is 4:2:1. ### Claim 17 (depends on 1) A complex crystal according to claim 1, wherein the derivative is the acridine having at least one side chain selected from the group consisting of amide group, a hydrazine group, an imino group, a guanidyl group, a halogen group, and an aliphatic hydrocarbon substituent having less than 10 carbons and an aromatic hydrocarbon substituent, the substituents being combined with the acridine directly or by way of sulfur or oxygen. ### Claim 18 (depends on 2) A complex crystal according to claim 2, wherein the derivative is the pyrazino (2,3-f) phenanthroline or the dipyrido (3,2-a; 2',3'-c) phenazine having at least one side chain selected from the group consisting of an amide group, a hydrazine group, an imino group, a guanidyl group, a halogen group, and an aliphatic hydrocarbon substituent having less than 10 carbons and an aromatic hydrocarbon substituent, the substituents being combined with the pyarzino (2,3-f) phenanthroline or the dipyrido (3,2-a; 2',3'-c) phenazine directly, or by way of sulfur or oxygen. ### Claim 19 A complex crystal consisting of: anions of triiodine arranged linearly; cations of acridine or a derivative thereof having a basic property; and anions of a Bronsted acid which neutralizes the basicity of acridine or a derivative thereof, the Bronsted acid being selected from the group consisting of sulfuric, hydrochloric, phosphoric, hydroiodic, sulfonic, monocarboxylic, and dicarboxylic acids; wherein the complex crystal has a structure in which the cations of the acridine or the derivative thereof and a chain of the anions of the triiodine are arranged alternately and orderly, and wherein the cations and the Bronsted acid anions form a neutral salt, so that an electron placed on the complex crystal is likely to move because of an interaction between the salt and the triiodine anions. ### Claim 20 A complex crystal consisting of: anions of triiodine arranged linearly; cations of pyazino (2,3-f) phenanthroline, dipyrido (3,2-a: 2',3'-c) phenazine, or a derivative thereof having a basic property; and anions of a Bronsted acid which neutralizes the basicity of pyrazino (2,3-f) phenanthroline, dipyrido (3,2-a; 2',3'-c) phenazine, or a derivative thereof, the Bronsted acid being selected from the group consisting of sulfuric, hydrochloric, phosphoric, hydroiodic, sulfonic, monocarboxylic, and dicarboxylic acids; wherein the complex crystal has a structure in which the cations of the pyrazino (2,3-f) phenanthroline, the dipyrido (3,2-a:2',3'-c) phenazine, or the derivative thereof and a chain of the anions of the triiodine are arranged alternately and orderly, and wherein the cations and the Bronsted acid anions form a neutral salt, so that an electron placed on the complex crystal is likely to move because of an interaction between the salt and the triiodine anions.