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Copyright WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2000. Supporting Information for: Off-the-Shelf Colorimetric Anion Sensors Hidekazu Miyaji and Jonathan L. Sessler*

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Page 1: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Copyright WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2000.

Supporting Information for:

Off-the-Shelf Colorimetric Anion Sensors

Hidekazu Miyaji and Jonathan L. Sessler*

Page 2: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourse

to Synthesis!

1,2-diaminoanthraquinone in dichloromethane (1 x 10-4

M). The color changed from yellow to dark purple by F-, to

red by Cl-, to reddish orange by Br-, to orange by I-, to

purple by H2PO4-, to orange by HSO4

-, to purple by AcO- and

BzO-, to red by CN-, to orange by NO3-, to orange by SCN-

(Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 3: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourse

to Synthesis!

1,2-diaminoanthraquinone in acetonitrile (1 x 10-4 M).

The color changed from orange to dark purple by F-, to red

by Cl-, to reddish orange by Br-, to purple by H2PO4-, to

purple by AcO- and BzO-, to red by CN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 4: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

1,2-diaminoanthraquinone in DMSO (1 x 10-4 M). The

color changed from red to green by F-, to purple by H2PO4-,

AcO- and BzO- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 5: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

1,8-diaminoanthraquinone in dichloromethane (1 x 10-4

M). The color changed from orange to reddish orange by F-,

H2PO4-, AcO-, BzO- and CN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 6: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

4-nitroaniline in dichloromethane (1 x 10-4 M).

The color changed from colorless to yellow by F-, H2PO4-,

AcO-, BzO- and CN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 7: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

4-nitro-1,2-phenylenediamine in dichloromethane (1 x

10-4 M). The color changed from pale yellow to orange by F-,

to intence yellow by Cl-, H2PO4-, AcO-, BzO- and CN-, to

yellow by Br-, HSO4-, NO3

- and SCN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 8: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

L-leucine-4-nitroanilide in dichloromethane (1 x 10-4

M). The color changed from colorless to intense yellow by

F-, to weak yellow by CN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 9: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

1-(4-nitrophenyl)-2-thiourea in DMSO (1 x 10-4 M). The

color changed from pale yellow to orange by F- and CN-, to

intense yellow by H2PO4-, AcO- and BzO- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 10: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

4-nitrophenol in dichloromethane (1 x 10-4 M). The

color changed from colorless to intense yellow by F-, H2PO4-,

AcO-, BzO- and CN-, to yellow by Cl- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO - CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 11: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

Alizarin in dichloromethane (1 x 10-4 M). The color

changed from yellow to blue by F-, H2PO4-, AcO-, BzO- and CN-

(Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 12: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

2,2’-bi(3-hydroxy-1,4-naphthoquinone) in

dichloromethane (1 x 10-4 M). The color changed from yellow

to purple by F-, CN-, to reddish orange by H2PO4-, AcO- BnO-,

to yellow by Cl-, HSO4-, NO3

- and SCN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 13: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

Acid blue 45 in DMSO (1 x 10-4 M). The color changedfrom blue to colorless by F-.

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 14: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

Naphthol AS in dichloromethane (1 x 10-4 M). The color

changed from colorless to fluorescent yellow by F-, H2PO4-,

AcO-, BzO- and CN- (Anion: 100 equiv.).

I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Cl- Br-

Page 15: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

9(10H)-acridone in DMSO (1 x 10-4 M). The color

changed from colorless to fluorescent yellow by F-, H2PO4-,

AcO- and CN- (Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-

Page 16: Off-the-Shelf Colorimetric Anion Sensors - Wiley-VCH - … Anion Sensors Finding Systems that Sense Anions without Recourse to Synthesis! 1,2-diaminoanthraquinone in dichloromethane

Off-the-Shelf Anion Sensors

Finding Systems that Sense Anions without Recourseto Synthesis!

Direct yellow 50 in DMSO (1 x 10-4 M). The color

changed from yellow to red by F-, to orange by H2PO4- and CN-

(Anion: 100 equiv.).

Cl- Br- I- H2PO4- HSO4

-

AcO- CN- NO3- SCN- ClO4

-

none F-

BzO-