Bromonaphthalimide compounds and phosphorescent liquid formulation thereof

Patent metadata

Field	Value
Publication number	US-11040946-B2
Application number	US-201916712265-A
Country	US
Kind code	B2
Filing date	Dec 12, 2019
Priority date	Oct 31, 2019
Publication date	Jun 22, 2021
Grant date	Jun 22, 2021

Abstract

The present invention provides a large scale paintable formulation of bromonapthalimide derivative compounds of formula (I) that shows phosphorescence in liquid state at 25-30° C. as well as their use as an indicator of temperature change in a visually enabled temperature measuring device.

First claim

We claim:

1. A compound of formula 1(e)

[6-bromo-2-(tricosan-12-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione]

wherein R=

wherein the compound is a pure, pale yellow solid.

2. The compound as claimed in claim 1 , wherein the compound exhibits liquid state phosphorescence at 20-30° C. in air.

3. A process for the preparation of a compound of formula 1(e)

comprising the steps of:
i) charging compound 6-bromo-1H,3H-benzo[de]isochromene-1,3-dione of formula 1, pentacosan-13-amine in alcohol solvent to obtain a reaction mass;

ii) heating the reaction mass as obtained in step (i) at a temperature in the range of 70-160° C. followed by maintaining the reaction mixture at 70-160° C. for a period in the range of 8-15 hr under argon atmosphere to obtain a reaction mass;
iii) cooling the reaction mass as obtained in step (ii) at a temperature in the range of 20-30° C. followed by filtering and washing with water to obtain a solid;
iv) drying the solid as obtained in step (iii) under vacuum to afford the compound of formula (1e) as a pure, pale yellow solid.

4. The process as claimed in claim 3 , wherein the reaction mixture is maintained at 160° C. for a period of 8 hr.

5. The process as claimed in claim 4 , wherein the alcohol solvent is selected from the group consisting of methanol, ethanol, isopropyl alcohol, n-propanol, n-butanol, ethylene glycol and mixtures thereof.

6. A paintable formulation exhibiting phosphorescence at 20-30° C. in neat form comprising the compound of formula 1(e) as claimed in claim 1 .

7. The paintable formulation as claimed in claim 6 , further comprising a doping with carbonyl groups.

8. The paintable formulation as claimed in claim 7 , wherein the carbonyl groups are introduced with the compounds benzene-1,3,5-tricarbaldehyde and terephthalaldehyde.

Assignees

• Council Scient Ind Res

Inventors

• Sukumaran Santhosh Babu
• Goudappagouda

Classifications

• C07D221/14 Primary

  Aza-phenalenes, e.g. 1,8-naphthalimide · CPC title

• G01K11/16

  of organic materials · CPC title

• G01K3/04

  in respect of time · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title