Color matched and bright fluorescent materials composed of small-molecule ionic lattices
The present disclosure concerns the design, formulations, preparations and optical properties of compounds of Formulas (I) and (VI): (charged dye m+ ) x ·(counterion n− ) y ·(counterion receptor) z (I) and (charged dye m− ) x ·(counterion n+ ) y ·(counterion receptor) z (VI). The charged dye m+ is a cationic dye, counterion n− is an anion, and counterion receptor is a binding ligand for the counterion n− , wherein m, n, x and y are integers greater than or equal to 1, and products of x·n and m·y are identical for formula (I). The charged dye m− is a anionic dye, counterion n+ is a cation, and counterion receptor is a binding ligand for the counterion n+ , wherein m, n, x and y are integers greater than or equal to 1, and products of x·n and m·y are identical for formula (VI).
1. A compound of Formula (I):
(charged dye m+ ) x ·(counterion n− ) y ·(counterion receptor) z (I),
wherein charged dye m+ is a cationic dye, counterion n− is an anion, and counterion receptor is a binding ligand for counterion n− ,
wherein m, n, x, y, and z are integers greater than or equal to 1 and products of x·n and m·y are identical,
wherein the counterion receptor is a heteromacrocycle selected from Formulas (B.1), (B.2), and (B.3):
or a combination thereof, wherein R′ of Formula (B.3) are identical and are selected from a group consisting of alkyl, alkenyl, alkoxy, aryl, heteroaryl, heterocycle, and substituted forms of alkenyl, alkoxy, aryl, heteroaryl, and heterocycle groups.
2. The compound according to claim 1 , wherein the cationic dye has a light-absorbing unit or both a light-absorbing unit and a light emissive unit.
3. The compound of claim 1 , wherein the cationic dye is selected from a group of dye classes consisting of cationic styryls, cationic xanthenes, cationic trianguleniums, cationic oxazines, triarylmethanes, cationic cyanines, cationic acridines, cationic fluoronones, cationic phenanthridines, cationic polyaromatic hydrocarbons, cationic imides, cationic BODIPYs, cationic coumarins, and cationic squaraines, or a combination thereof.
4. The compound of claim 1 , wherein the cationic dye is selected from the group consisting of the following members:
5. The compound of claim 1 , wherein the cationic dye is selected from the group consisting of the following members:
6. The compound of claim 1 , wherein the heteromacrocycle is selected from Formulas (B.1) or (B.2).
7. The compound according to claim 1 , wherein the anion is selected from the group consisting of BF 4 − , ClO 4 − , PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 − , AsO 4 3− , HAsO 4 2− , H 2 AsO 4 − , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 −2 , HSO 4 − , Cl − , Br − , I − , cyanide, BrO 4 − , IO 4 − , F − , HF 2 − , TcO 4 − , RPO 4 2− , R 2 PO 4 − , RSO 3 − , SCN − , N 3 − , I 3 − , CO 3 2− , HCO 3 − , P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− , H 3 P 2 O 7 − , RBF 3 − , wherein R comprises a substituent.
8. The compound according to claim 1 , provided that the anion is not F5-TPB − ; tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; tetrakis[3,5-bis(1,1,1,3,3,3-hexafluoro-2-methoxy-2-propyl)phenyl]borate; Ar 4 B − , wherein Ar is aryl; TRISPHAT − ; or BINPHAT − .
9. The compound according to claim 1 , wherein the cationic dye comprises a light-absorbing unit.
10. The compound according to claim 9 , wherein the cationic dye absorbs light at a wavelength longer than the absorption wavelength of a complex formed between the counterion n− and the counterion receptor.
11. The compound according to claim 9 , wherein the compound comprises a light-absorbing unit having light-absorbing properties that reproduce the light absorbing properties (absorption band position and width) of the cationic dye alone under dilute conditions.
12. The compound according to claim 1 , wherein the cationic dye comprises a light-absorbing unit and a light emissive unit.
13. The compound according to claim 12 , wherein the cationic dye absorbs and emits light at a wavelength longer than the absorption wavelength of a complex formed between the counterion n− and the counterion receptor.
14. The compound according to claim 12 , wherein an electronic property of the cationic dye and the counterion receptor complex does not produce partial or full electron transfer, photo induced electron transfer between the cationic dye and the counterion receptor, or does not produce a new absorption or emission band.
15. A formulation comprising a compound of according to claim 1 .
16. A method of detecting a substance, comprising:
contacting the substance with the compound according to claim 1 to form a mixture; and
measuring a change in at least one spectral property in the compound of the mixture as a result of the contacting step relative to the substance alone or the compound alone,
wherein the substance is detected by the change in at least one spectral property of the compound as a result of the measuring step with the mixture.
17. The compound according to claim 9 , wherein Formula (I) is Formula (I-X1).
18. The compound according to claim 9 , wherein Formula (I) is Formula (I-X2)
19. The compound according to claim 12 , wherein Formula (I) is Formula (I-X1).
20. The compound according to claim 12 , wherein Formula (I) is selected from Formula (I-X2), Formula (I-X3), and Formula (I-X4):