Polymers with high internal free volume

• US 6,783,814 B2
• Filed: 08/21/2001
• Issued: 08/31/2004
• Est. Priority Date: 08/21/2000
• Status: Expired due to Term

• Current Assignee: Massachusetts Institute of Technology
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Zhu, Zhengguo, Swager, Timothy M., Long, Timothy M.
• Primary Examiner(s): Truong, Duc
• Application Number:
  US09/935,060
• Publication Number:
  US 20020150697A1
• Time in Patent Office: 1,106 Days
• Field of Search: 428/11, 428/1, 525/63, 252/299.01, 349/1
• US Class Current: 428/11
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C08G 61/10 only aromatic carbon atoms, e.g. polyphenylenes
• CPC Class Codes: C08G 61/12 Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
• CPC Class Codes: C08L 101/12 characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity liquid crystal materials or compositions C09K19/00
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 19/38 Polymers
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
• CPC Class Codes: C09K 2323/03 Viewing layer characterised by chemical composition
• CPC Class Codes: H01B 1/12 organic substances organic macromolecular compounds or compositions C08
• CPC Class Codes: H01L 21/02118 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC polymers per se C08G, photoresist per se G03F
• CPC Class Codes: H01L 21/312 Organic layers, e.g. photoresist H01L21/3105, H01L21/32 take precedence; photoresists per se G03C
• CPC Class Codes: H10K 85/154 Ladder-type polymers
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/653 comprising only oxygen as heteroatom

Abstract

Shape-persistent organic materials, including polymers, with large degrees of interior free volume are described, along with behaviors and phenomena enabled by their unique properties. One class of such a material is built up from triptycene base moieties wherein three benzene rings are bridged together about a [2.2.2] tricyclic ring system. These units can be assembled into discreet molecules and polymers. These materials and/or formulations thereof with liquid crystals or polymers are useful for the complexation of chemicals and/or polymers; they have very low dielectric constants for use as coatings in dielectric circuits, they provide additional ordering mechanisms in liquid crystals, and they display unusual mechanical responses when subjected to electrochemical, chemical, or mechanical stimuli.

Claims

1. A composition comprising:

a chromophore;

a shape-persistent molecule having at least 20% free volume; and

a host material within which the shape-persistent molecule self-orients.

2. A composition as in claim 1, where the shape-persistent molecule includes at least two aromatic rings, each parallel to a common axis in a lowest energy state of the composition.

3. A composition as in claim 1, wherein the chromophore is bonded to the shape-persistent molecule.

4. A composition as in claim 1, wherein the chromophore is a fluorescent entity.

5. A composition as in claim 1, further comprising a liquid crystalline species.

6. A composition as in claim 5, comprising:

a plurality of liquid crystalline species, each having a primary axis aligned so as to together define an average axis of the liquid crystalline species primary axes; and

a plurality of chromophores each having a primary axis aligned so as to together define an average axis of the chromophore primary axes,

wherein the alignment of the individual chromophores relative to the average axis of the chromophore primary axes includes less variation than the alignment of the individual liquid crystalline species relative to the average axis of the liquid crystalline species primary axes.

7. An article defining a size-exclusion article, comprising a composition as in claim 1.

8. An article comprising an electrode, and a composition as in claim 1 associated with the electrode.

9. A composition comprising a first component as in claim 1 and a second component that has a high molecular weight linear polymer such that the composition has superior strength compared to a composition that lacks the first component.

10. A composition as in claim 9 wherein the first component comprises an iptycene.

11. A composition as in claim 1, comprising polymerizable groups.

12. A composition as in claim 1, wherein the chromophore is a liquid crystal.

13. A composition as in claim 1, wherein the host material comprises a plurality of liquid crystalline species, each having a primary axis aligned so as to together define an average axis of the liquid crystalline species primary axes, wherein the chromophore has a transition moment that is essentially parallel to the average axis of the liquid crystalline species primary axes.

14. A composition as in claim 1, wherein the host material comprises a plurality of liquid crystalline species, each having a primary axis aligned so as to together define an avenge axis of the liquid crystalline species primary axes, wherein the chromophore has a transition moment that is essentially perpendicular to the average axis of the liquid crystalline species primary axes.

15. A composition as in claim 1, further comprising a plurality of liquid crystalline species, wherein the chromophore self-orients relative to the liquid crystalline species.

16. A molecule as in claim 1 wherein the dichroic molecule exhibits a greater order parameter than the liquid crystal host.

17. A molecule as in claim 1 wherein the dichroic molecule is fluorescent.

18. A molecule as in claim 1 wherein first component is an iptycene.