Long wavelength voltage sensitive dyes

Patent metadata

Field	Value
Publication number	US-11169156-B2
Application number	US-201615745044-A
Country	US
Kind code	B2
Filing date	Jul 28, 2016
Priority date	Jul 28, 2015
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

The disclosure provides for provides for water-soluble near-infra red (NIR) emissive compounds, processes of making the compounds thereof, and use of the compounds therein.

First claim

What is claimed is:

1. A compound comprising the structure of Formula II:

wherein,
A 1 is selected from SiH 2 , SiHR′, or SiR′ 2 , wherein R′ is selected from the group consisting of D, optionally substituted FG, optionally substituted (C 1 -C 12 )alkyl, optionally substituted (C 1 -C 11 )heteroalkyl, optionally substituted (C 1 -C 12 )alkenyl, optionally substituted (C 1 -C 11 )heteroalkenyl, optionally substituted (C 1 -C 12 )alkynyl, and optionally substituted (C 1 -C 11 )heteroalkynyl;
X 1 -X 11 are independently selected from N or C, wherein when an X group is an N, then the R group is absent; and
R 1 -R 15 are independently selected from H, D, optionally substituted FG, optionally substituted (C 1 -C 12 )alkyl, optionally substituted (C 1 -C 11 )heteroalkyl, optionally substituted (C 1 -C 12 )alkenyl, optionally substituted (C 1 -C 11 )heteroalkenyl, optionally substituted (C 1 -C 12 )alkynyl, optionally substituted (C 1 -C 11 )heteroalkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, optionally substituted mixed ring system, wherein one or more adjacent R groups can be linked together to form one or more substituted rings selected from the group comprising cycloalkyl, cycloalkenyl, heterocycle, aryl, and mixed ring system,
W 1 is a molecular wire moiety; and
wherein one of R 1 or R 5 is a sulfonate group.

2. The compound of claim 1 , wherein the compound comprises the structure of Formula II(a):

wherein,
L 1 is selected from the group consisting of:

and any combination of the foregoing;
wherein
A 1 is selected from SiH 2 , SiHR′, or SiR′ 2 ;
A 2 -A 8 are each independently selected from CH 2 , CHR′, CR′ 2 , NH, O, S, Se, Te, SiH 2 , SiHR′, SiR′ 2 , GeH 2 , GeHR′, GeR′ 2 , SnH 2 , SnHR′, SnR′ 2 , PbH 2 , PbHR′, or PbHR′ 2 , wherein R′ is selected from the group consisting of D, optionally substituted FG, optionally substituted (C 1 -C 12 )alkyl, optionally substituted (C 1 -C 11 )heteroalkyl, optionally substituted (C 1 -C 12 )alkenyl, optionally substituted (C 1 -C 11 )heteroalkenyl, optionally substituted (C 1 -C 12 )alkynyl, and optionally substituted (C 1 -C 11 )heteroalkynyl;
X 1 , X 2 , and X 4 -X 42 are independently selected from N or C, wherein when an X group is an N, then the R group is absent;
R 1 , R 2 , and R 4 -R 54 are independently selected from H, D, optionally substituted FG, optionally substituted (C 1 -C 12 )alkyl, optionally substituted (C 1 -C 11 )heteroalkyl, optionally substituted (C 1 -C 12 )alkenyl, optionally substituted (C 1 -C 11 )heteroalkenyl, optionally substituted (C 1 -C 12 )alkynyl, optionally substituted (C 1 -C 11 )heteroalkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, optionally substituted mixed ring system, wherein one or more adjacent R groups can be linked together to form one or more substituted rings selected from the group comprising cycloalkyl, cycloalkenyl, heterocycle, aryl, and mixed ring system;
wherein one of R 1 or R 5 is a sulfonate group; and

n 1 -n 8 are independently an integer selected from 0 to 10.

3. The compound of claim 2 , wherein the compound comprises the structure of Formula II(b):

wherein,
X 1 , X 2 , and X 4 -X 20 are independently selected from N or C, wherein when an X group is an N, then the R group is absent;
R 2 , R 4 -R 11 , and R 16 -R 26 are independently selected from H, D, optionally substituted FG, optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 5 )heteroalkyl, optionally substituted (C 1 -C 6 )alkenyl, optionally substituted (C 1 -C 5 )heteroalkenyl, optionally substituted (C 1 -C 6 )alkynyl, optionally substituted (C 1 -C 5 )heteroalkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, optionally substituted mixed ring system, wherein one or more adjacent R groups can be linked together to form one or more substituted rings selected from the group comprising cycloalkyl, cycloalkenyl, heterocycle, aryl, and mixed ring system; and
n 1 is an integer from 0 to 5.

4. The compound of claim 3 , wherein the compound comprises the structure of Formula II(c):

wherein,
R 16 , R 17 , R 19 and R 20 are independently selected from H, D, optionally substituted FG, optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 5 )heteroalkyl, optionally substituted (C 1 -C 6 )alkenyl, optionally substituted (C 1 -C 5 )heteroalkenyl, optionally substituted (C 1 -C 6 )alkynyl, optionally substituted (C 1 -C 5 )heteroalkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, optionally substituted mixed ring system, wherein one or more adjacent R groups can be linked together to form one or more substituted rings selected from the group comprising cycloalkyl, cycloalkenyl, heterocycle, aryl, and mixed ring system;
n 1 is an integer from 0 to 5.

5. The compound of claim 4 , wherein the compound comprises the structure of:

6. The compound of claim 1 , wherein the compound has one or more of the following characteristics:
the compound emits far red to near infrared light upon excitation with incident light;
the compound is water soluble;
the compound exhibits minimal solvatochromism;
the compound does not undergo spirocyclization in either acidic or basic environments; and/or
the compound can undergo photoinduced electron transfer.

7. The compound of claim 6 , wherein the compound is characterized by emitting far red to near infrared light upon excitation with incident light; is water soluble; exhibits minimal solvatochromism; does not undergo spirocyclization in either acidic or basic environments; and can undergo photoinduced electron transfer.

Assignees

• Univ California

Inventors

• Miller Evan W
• Huang Yi-Lin
• Walker Alison S

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C09B23/0066

  the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid) · CPC title

• G01N33/582 Primary

  with fluorescent label · CPC title

• G01N2015/1006

  for cytology · CPC title

• C09B69/06

  of cationic dyes with organic acids {or with inorganic complex acids} · CPC title