Cyclic delocalized cations connected by spacer groups

• US 6,531,241 B1
• Filed: 07/07/2000
• Issued: 03/11/2003
• Est. Priority Date: 07/08/1999
• Status: Expired due to Fees

• Current Assignee: Covalent Associates, Inc.
• Original Assignee: Covalent Associates, Inc.
• Inventors: McEwen, Alan B.
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US09/611,787
• Time in Patent Office: 977 Days
• Field of Search: 508/221, 252/62.2, 252/500, 429/46, 429/212, 429/213, 361/500, 361/503, 361/504
• US Class Current: 429/499
• CPC Class Codes: C07D 213/06 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/54 having two double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 237/08 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 241/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 263/32 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/22 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C22B 3/36 Heterocyclic compounds C22B3/34 takes precedence
• CPC Class Codes: H01B 1/122 Ionic conductors
• CPC Class Codes: H01G 11/62 characterised by the solute, e.g. salts, anions or cations therein
• CPC Class Codes: H01M 10/0525 Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
• CPC Class Codes: H01M 10/0568 characterised by the solutes
• CPC Class Codes: H01M 6/166 by the solute
• CPC Class Codes: Y02E 60/10 Energy storage using batteries
• CPC Class Codes: Y02E 60/13 Energy storage using capacitors
• CPC Class Codes: Y02P 10/20 Recycling

Abstract

Cyclic delocalized cations joined together by spacer groups, with anions of equal number to cations to maintain charge neutrality, are disclosed. These spacer groups may be organic or inorganic in origin and may vary in length. The spacer groups may be saturated, containing single bonds, or may be unsaturated, containing double and triple bonds. With appropriate design these materials can have melting and glass transition temperatures below, around, and above room temperature. The lyophobic character of these materials may be adjusted, providing unique properties. These materials are well suited for use as electrolytes, lubricants, solvents for extractions and for running reactions, biphase catalysis media, media for electroluminescent devices.

Claims

1. A salt comprising two or more delocalized cations, said cations being separated by spacer groups, wherein said cations are selected from the group consisting of:

wherein R₁, R₂, R₃, R₄, R₅, and R₆ are either H, F, or separate alkyl groups having 1-25 carbon atoms;

or any two of R₁-R₆ can be joined together to constitute a unitary alkylene radical forming one or more ring structures converging on the cyclic delocalized aromatic ring; and

wherein the alkyl groups or alkylene radicals may be substituted with electron withdrawing groups; and

wherein said salt also comprises anions in appropriate number to maintain charge neutrality, and wherein said anion is a polyatomic anion having a van der Waals volume exceeding 100 A³.

2. The salt of claim 1 wherein said salt is hydrophobic.

3. The salt of claim 1 wherein said salt is hydrophilic.

4. The salt of claim 1 wherein all cations are the same.

5. The salt of claim 1 which comprises 2 or more different cations.

6. The salt of claim 1 wherein said spacer groups contain from one to thirty-five repeating units having saturated or unsaturated bonds.

7. The salt of claim 1 wherein said spacer groups contain inorganic atoms.

8. The salt of claim 1 wherein said anions are connected to each other resulting in separate linear chains of anions and cations.

9. The salt of claim 1 wherein said anions are connected in a tethered fashion to the linear cation chain.

10. The salt of claim 1 wherein said anions are selected from the group consisting of PF₆, Im, Beti, BAI, TAM and Me.

11. The salt of claim 1 wherein said cation comprises alkyl groups at all non-linking positions, said alkyl groups containing 1-25 carbon atoms.

12. The salt of claim 1 wherein said salt is a zwitterion.

13. A process for using the salt of claim 1, said process comprising adding said salt to a device selected from the group consisting of electrochemical storage devices, electroluminescent devices and electrochromic devices to serve as the electrolyte of said device.