Modular supramolecular approach for co-crystallization of donors and acceptors into ordered networks

Patent metadata

Field	Value
Publication number	US-9449731-B2
Application number	US-201213476974-A
Country	US
Kind code	B2
Filing date	May 21, 2012
Priority date	May 20, 2011
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

Organic charge-transfer (CT) co-crystals in a mixed stack system are disclosed, wherein a donor molecule (D) and an acceptor molecule (A) occupy alternating positions (DADADA) along the CT axis. A platform is provided which amplifies the molecular recognition of donors and acceptors and produces co-crystals at ambient conditions, wherein the platform comprises (i) a molecular design of the first constituent (α-complement), (ii) a molecular design of the second compound (β-complement), and (iii) a solvent system that promotes co-crystallization.

First claim

What is claimed is:

1. An organic charge-transfer (CT) co-crystal consisting essentially of an electron acceptor molecule (A) and an electron donor molecule (D), such that one of (A) and (D) is incorporated into the other of (A) and (D) through molecular linkages in a solvent system to form a co-crystalline supramolecular network, wherein one or more of the molecular linkages between the (A) and (D) uses adaptive intermolecular recognition to form the one or more molecular linkages, the co-crystal characterized by having a crystal superstructure comprising a mixed stack lattice (DADADA) and a topological hydrogen-bonded network, said organic CT co-crystal wherein A is selected from the group consisting of

and D is selected from the group consisting of

2. The organic CT co-crystal according to claim 1 , wherein A is a diimide.

3. The organic CT co-crystal according to claim 1 , wherein the solvent system is one or more organic solvents.

4. The organic CT co-crystal according to claim 3 , wherein the solvent system is selected from the group consisting of dichloroethane/diethyl ether and N-methylpyrrolidone.

5. The organic CT co-crystal according to claim 1 , wherein one of the (A) and (D) has a substituent that is a diethylene glycol moiety.

6. The organic CT co-crystal according to claim 1 , wherein the hydrogen-bonded network comprises interstack and intrastack hydrogen bonds.

7. The organic CT co-crystal according to claim 1 , wherein the co-crystal is devoid or substantially devoid of solvent.

8. The organic CT co-crystal according to claim 1 , wherein one of the (A) and (D) has a substituent that has one or more hydrogen-bonding recognition sites.

9. The organic CT co-crystal according to claim 8 , wherein the one or more hydrogen-bonding recognition sites is independently selected from the group consisting of amino, carbonyl, ether and hydroxyl moieties.

10. The organic CT co-crystal according to claim 1 , wherein the (A) has at least four substituents.

11. The organic CT co-crystal according to claim 10 , wherein the (D) has at least one substituent.

12. The organic CT co-crystal according to claim 1 , wherein the co-crystal is grown in the dark, under ambient conditions.

13. The organic CT co-crystal according to claim 12 , wherein the co-crystal is grown using liquid diffusion.

14. The organic CT co-crystal according to claim 1 selected from the group consisting of

15. The organic CT co-crystal according to claim 1 , wherein the co-crystal has a packing motif that is a crossed stack.

Assignees

• Stupp Samuel I
• Stoddart J Fraser
• Shveyd Alex K
• Tayi Alok S
• Sue Andrew C H
• Narayanan Ashwin
• Univ Northwestern

Inventors

• Stupp Samuel I
• Stoddart J Fraser
• Shveyd Alex K
• Tayi Alok S
• Sue Andrew C H
• Narayanan Ashwin

Classifications

• C07D487/14

  Ortho-condensed systems · CPC title

• H01B1/121 Primary

  Charge-transfer complexes · CPC title