Compound and dimer complex embodiments for supramolecular sensing

Patent metadata

Field	Value
Publication number	US-11629128-B2
Application number	US-202016911250-A
Country	US
Kind code	B2
Filing date	Jun 24, 2020
Priority date	Jun 25, 2019
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

Disclosed herein are embodiments of a compound that can be used as a supramolecular sensor for determining the presence of analytes (e.g., illicit drugs), and for identifying and/or quantifying the analytes. Also disclosed herein is a parallel synthesis method for making compound embodiments, as well as method embodiments for using the compound embodiments. Array embodiments comprising one or more compound embodiments disclosed herein also are described.

First claim

We claim:

1. A dimer complex, comprising:
a first compound having a structure according to Formula I; and
a second compound having a structure according to Formula I;

wherein Formula I is

wherein
each A independently is selected from C(O)H; CH 2 OH; or —SO 3 R′, wherein each R′ independently is H or a counterion; or linker′-Ring B′ , wherein linker′ is aliphatic or heteroaliphatic and Ring B′ is a ring system capable of producing a detectable signal;
each E independently is selected from —SO 3 R′, wherein each R′ independently is H or a counterion;
each J independently is selected from —SO 3 R′, wherein each R′ independently is H or a counterion;
each of X 1 , X 2 , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , CH 2 SCH 2 , or NR b wherein each R b independently is hydrogen, aliphatic, heteroaliphatic, or aromatic;
each R independently is H, aliphatic, or a counterion;
the linker group has a structure satisfying a Formula IA

wherein each L and L′ independently is CH or N; M is NH; q is an integer selected from 1 to 3;
and r is 0 or 1;
the B ring comprises an N-functionalized nitrogen-containing ring system, a 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or a nitrobenzo[c][1,2,5]oxadiazole functional group; and
each of n, m, and p independently is an integer selected from 1 to 3;

and further wherein
(i) the first compound and the second compound chemically interact to form the dimer complex and wherein the dimer complex does not emit a detectable signal or wherein the dimer complex emits a dimer detectable signal that is different from any detectable signal provided by the first compound, the second compound, or both; and
(ii) the first compound has a structure that is different from the second compound.

2. The dimer complex of claim 1 , wherein the linker′ group has a structure satisfying a Formula IA

wherein each L and L′ independently is CH or N; M is NH; q is an integer selected from 1 to 3; and r is 0 or 1.

3. The dimer complex of claim 1 , wherein the Ring B group comprises the N-functionalized nitrogen-containing ring system.

4. The dimer complex of claim 1 , wherein the Ring B′ group comprises an N-functionalized nitrogen-containing ring system, a 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or a nitrobenzo[c][1,2,5]oxadiazole functional group.

5. The dimer complex of claim 1 , wherein the Ring B and/or the Ring B′ groups independently are selected from:

6. The dimer complex of claim 1 , wherein each of the first compound and the second compound independently has a structure according to any one or more of Formulas II-V

wherein n is an integer selected from 0, 1, or 2; m is an integer selected from 1, 2, or 3; each R independently is H or an aliphatic group; each of X 1 , X 2 , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , or CH 2 SCH 2 ; each A and each of E and J independently is SO 3 H or SO 3 — balanced with a counterion provided by an aqueous solution, buffered aqueous solution, or any other counterion that may exist in the environment in which the compound is provided; each of Q and T independently is N or CH; and U comprises the N-functionalized nitrogen-containing ring system, the 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or the nitrobenzo[c][1,2,5]oxadiazole functional group;

wherein n independently is an integer selected from 0, 1, or 2; each R independently is H or an aliphatic group; each of X 1 , X 2 , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , or CH 2 SCH 2 ; each of E and J independently is SO 3 H or SO 3 — balanced with a counterion provided by an aqueous solution, buffered aqueous solution, or any other counterion that may exist in the environment in which the compound is provided; T is N or CH; V is NH; and U comprises the N-functionalized nitrogen-containing ring system, the 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or the nitrobenzo[c][1,2,5]oxadiazole functional group;

wherein each of m and m′ independently is an integer selected from 1, 2, or 3; each R independently is H or an aliphatic group; each of X 1 , X 2 , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , or CH 2 SCH 2 ; each of E and J independently is SO 3 H or SO 3 — balanced with a counterion provided by an aqueous solution, buffered aqueous solution, or any other counterion that may exist in the environment in which the compound is provided; each of Q, T, Q′, and T′ independently is N or CH; and U and U′ independently comprises the N-functionalized nitrogen-containing ring system, the 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or the nitrobenzo[c][1,2,5]oxadiazole functional group; or

wherein m independently is an integer selected from 1, 2, or 3; each R independently is H or an aliphatic group; each of X 1 , X 2 , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , or CH 2 SCH 2 ; each of E and J independently is SO 3 H or SO 3 — balanced with a counterion provided by an aqueous solution, buffered aqueous solution, or any other counterion that may exist in the environment in which the compound is provided; each of Q and T independently is N or CH; U comprises the N-functionalized nitrogen-containing ring system, the 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or the nitrobenzo[c][1,2,5]oxadiazole functional group; and A is C(O)H or CH 2 OH.

7. The dimer complex of claim 1 , wherein each of the first compound and the second compound independently has structure according to Formula VA

wherein m independently is an integer selected from 1, 2, or 3; each R independently is H or an aliphatic group; each of X 1 , X 2 , X 2′ , X 3 , and X 4 independently is CH 2 , O, S, CH 2 OCH 2 , or CH 2 SCH 2 ; each of E and J independently is SO 3 H balanced with a counterion provided by an aqueous solution, buffered aqueous solution, or any other counterion that may exist in the environment in which the compound is provided; each of Q and T independently is N or CH; U comprises the N-functionalized nitrogen-containing ring system, the 2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione functional group, or the nitrobenzo[c][1,2,5]oxadiazole functional group; and each of A and A′ independently is C(O)H or CH 2 OH.

8. The dimer complex of claim 1 , wherein each of the first compound and the second compound independently is selected from

Assignees

• Uvic Ind Partnerships Inc

Inventors

• Beatty Meagan
• Hof Fraser
• Selinger Allison

Classifications

• C07D221/06

  Ring systems of three rings · CPC title

• C07D285/06

  1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles · CPC title

• C07D263/56

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2 · CPC title

• G01N33/542

  with steric inhibition or signal modification, e.g. fluorescent quenching · CPC title

• C07D215/14

  Radicals substituted by oxygen atoms · CPC title