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Supplementary Information for

N-acylamino-pyridine-2,6-dione based heterocyclic dyes and their

oxidative ring-degradation under alkaline condition

Jiao Geng,a Dan Xu,a Xiao-Lei Zhao,a Ya-Nan Feng,b Hui-Fen Qian,b

Yuan Dai,a Wei Huanga, *

a State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of

Microstructures, School of Chemistry and Chemical Engineering, Nanjing University,

Nanjing, Jiangsu Province, 210093, P. R. China, Fax: +86-25-89682309, Tel.: +86-

25-89686526, E-mail: whuang@nju.edu.cnb College of Sciences, Nanjing Tech University, Nanjing, Jiangsu Province, 210009, P.

R. China

Contents Page Number

1. Dyeing performance evaluation data---------------------------------------------------S2

2. Scheme-------------------------------------------------------------------------------------S2

3. ESIMS--------------------------------------------------------------------------------S3-S7

4. TGADSC-----------------------------------------------------------------------------S7-S8

5. 1H NMR-------------------------------------------------------------------------------S9-S13

6. Perspective view of the packing structures-------------------------------------------S13

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016

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Table SI1 Dyeing performance evaluation data of dyes 46, together with five

commercially available C.I. Disperse Yellow dyes (114, 119, 126, 211 and 241) for

comparison.

Sublimation fastness

Washing fastness CA N T

Dipping fastness CA N T

Light fastness

Dye 4 5 5 5 5 5 5 5 6~7 24.50Dye 5 5 5 5 5 5 5 5 6~7 24.28Dye 6 5 5 5 5 5 5 5 6~7 24.63

C.I. Yellow 114 4 4~5 4~5 5 4 3~4 4~5 6~7 24.06C.I. Yellow 119 2 4 3~4 5 4~5 4~5 4~5 6~7 25.61C.I. Yellow 126 4 4~5 4~5 5 4 3~4 4~5 6~7 26.49C.I. Yellow 211 2~3 4 3~4 5 4~5 4~5 4~5 6~7 27.97C.I. Yellow 241 2 3~4 3~4 4~5 4~5 4~5 4~5 6~7 27.41

CA: cellulose acetate; Nnylon; Tterylene

R

R

O

O +H2N

CN

O

R

OH2N

CN

O

Rbase-H2O

NH

-H2O O

CNR

R

Scheme SI1. Conventional synthetic approach for pyridine-2,6-dione derivatives

in industry.

Name K/Smax

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Fig. SI1. ESIMS diagram of compound 1.

Fig. SI2. ESIMS diagram of compound 2.

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Fig. SI3. ESIMS diagram of compound 3.

Fig. SI4. ESIMS diagram of compound 4.

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Fig. SI5. ESIMS diagram of compound 5.

Fig. SI6. ESIMS diagram of compound 6.

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Fig. SI7. ESIMS diagram of compound 7.

Fig. SI8. ESIMS diagram of compound 8.

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Fig. SI9. ESIMS diagram of compound 9.

Fig. SI10. TGADSC diagram of compound 4.

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Fig. SI11. TGADSC diagram of compound 5.

Fig. SI12. TGADSC diagram of compound 6.

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Fig. SI13. 1H NMR diagram of compound 1.

Fig. SI14. 1H NMR diagram of compound 2.

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Fig. SI15. 1H NMR diagram of compound 3.

Fig. SI16. 1H NMR diagram of compound 4.

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Fig. SI17. 1H NMR diagram of compound 5.

Fig. SI18. 1H NMR diagram of compound 6.

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Fig. SI19. 1H NMR diagram of compound 7.

Fig. SI20. 1H NMR diagram of compound 8.

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Fig. SI21. 1H NMR diagram of compound 9.

Fig. SI22. Different packing fashions of dyes 4·CH3CN (top) and 5 (bottom).

3.134(4) Å3.134(4) Å

3.243(2) Å