supplementary information for · s1 supplementary information for n-acylamino-pyridine-2,6-dione...
TRANSCRIPT
S1
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: [email protected] 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
S2
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
S3
Fig. SI1. ESIMS diagram of compound 1.
Fig. SI2. ESIMS diagram of compound 2.
S4
Fig. SI3. ESIMS diagram of compound 3.
Fig. SI4. ESIMS diagram of compound 4.
S5
Fig. SI5. ESIMS diagram of compound 5.
Fig. SI6. ESIMS diagram of compound 6.
S6
Fig. SI7. ESIMS diagram of compound 7.
Fig. SI8. ESIMS diagram of compound 8.
S7
Fig. SI9. ESIMS diagram of compound 9.
Fig. SI10. TGADSC diagram of compound 4.
S8
Fig. SI11. TGADSC diagram of compound 5.
Fig. SI12. TGADSC diagram of compound 6.
S9
Fig. SI13. 1H NMR diagram of compound 1.
Fig. SI14. 1H NMR diagram of compound 2.
S10
Fig. SI15. 1H NMR diagram of compound 3.
Fig. SI16. 1H NMR diagram of compound 4.
S11
Fig. SI17. 1H NMR diagram of compound 5.
Fig. SI18. 1H NMR diagram of compound 6.
S12
Fig. SI19. 1H NMR diagram of compound 7.
Fig. SI20. 1H NMR diagram of compound 8.
S13
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