Supporting InformationThe deep eutectic melt of sorbitol and metformin hydrochloride: Synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-diones and their photophysical properties

Kurosh Rad-Moghadam*, Seyyed Ali Reza Mousazadeh Hassani and Saeedeh Toorchi RoudsariChemistry department, Univrsity of Guilan, Rasht 41335-1914; radmm@guilan.ac.ir

ContentsS1 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of

Sorbitol:MetHCl (2:1)S2 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of

Sorbitol:MetHCl (3:1)S3 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of

Sorbitol:MetHCl (4:1)S4 The IR spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-dione (4d)S5 The 1H NMR spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-

dione in DMSO-d6 + D2O (4d)S6 The 1H NMR spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-

dione in DMSO-d6 (4d)S7 The 13C NMR spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-

dione (4d)S8 The Mass spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-dione

(4d)S9 The IR spectrum of 2-amino-3-(4-bromophenyl)naphtho[2,3-b]furan-4,9-dione (4g)S10 The 1H NMR spectrum of 2-amino-3-(4-bromophenyl)naphtho[2,3-b]furan-4,9-dione

(4g)S11 The 13C NMR spectrum of 2-amino-3-(4-bromophenyl)naphtho[2,3-b]furan-4,9-dione

(4g)

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

S12 The Mass spectrum of 2-amino-3-(4-bromophenyl)naphtho[2,3-b]furan-4,9-dione (4g)S13 The 1H NMR spectrum of 3:1 S:MetHClS13 The 1H NMR spectrum of 3:1 S:MetHClS13 The 1H NMR spectrum of 3:1 S:MetHClS13 The 1H NMR spectrum of 3:1 S:MetHClS14 The 13C NMR spectrum of 3:1 S:MetHClS14 The 13C NMR spectrum of 3:1 S:MetHClS15 The absorption (dashed) and emission (solid) spectra for compound (4b)

S16 The absorption (dashed) and emission (solid) spectra for compound (4c)

S17 The absorption (dashed) and emission (solid) spectra for compound (4d)

S18 The absorption (dashed) and emission (solid) spectra for compound (4e)

S19 The absorption (dashed) and emission (solid) spectra for compound (4f)

S20 The absorption (dashed) and emission (solid) spectra for compound (4g)

S21 The absorption (dashed) and emission (solid) spectra for compound (4h)

S22 The absorption (dashed) and emission (solid) spectra for compound (4i)

S1 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of Sorbitol:MetHCl (2:1)

S2 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of Sorbitol:MetHCl (3:1)

S3 Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) of Sorbitol:MetHCl (4:1)

S4 The IR spectrum of 2-amino-3-(4-

nitrophenyl)naphtho[2,3-b]furan-4,9-

dione (4d)

ONH2

O

O

NO2

S5 The1H NMR spectrum of 2-

amino-3-(4-nitrophenyl)

naphtho[2,3-b]furan-4,9-

dione in DMSO-d6 (4d)

S5 The 1H NMR spectrum of 2-

amino-3-(4-nitrophenyl)

naphtho[2,3-b]furan-4,9-dione

in DMSO-d6 (4d)

S6 The 1H NMR spectrum of 2-

amino-3-(4-nitrophenyl)

naphtho[2,3-b]furan-4,9-

dione in DMSO-d6 + D2O

(4d)

S7 The 13C NMR spectrum of

2-amino-3-(4-nitrophenyl)

naphtho[2,3-b]furan-4,9-

dione (4d)

S7 The 13C NMR spectrum of

2-amino-3-(4-nitrophenyl)

naphtho[2,3-b]furan-4,9-

dione (4d)

S8 The Mass spectrum of 2-amino-3-(4-nitrophenyl)naphtho[2,3-b]furan-4,9-dione (4d)

S9 The IR spectrum of 2-amino-

3-(4-bromophenyl)naphtho[2,3-

b]furan-4,9-dione (4g)

S10 The 1H NMR spectrum of 2-

amino-3-(4-bromophenyl)

naphtho[2,3-b]furan-4,9-dione

(4g)

S10 The 1H NMR spectrum of 2-

amino-3-(4-bromophenyl)

naphtho[2,3-b]furan-4,9-dione

(4g)

S11 The 13C NMR spectrum of

2-amino-3-(4-bromophenyl)

naphtha[2,3-b]furan-4,9-dione

(4g)

S11 The 13C NMR spectrum of

2-amino-3-(4-bromophenyl)

naphtha[2,3-b]furan-4,9-dione

(4g)

S12 The Mass spectrum of 2-amino-3-(4-bromophenyl) naphtha [2,3-b]furan-4,9-dione (4g)

S13 The 1H NMR spectrum of 3:1 S:MetHCl

S13 The 1H NMR spectrum of 3:1 S:MetHCl

S13 The 1H NMR spectrum of 3:1 S:MetHCl

S13 The 1H NMR spectrum of 3:1 S:MetHCl

S14 The 13C NMR spectrum of 3:1 S:MetHCl

S14 The 13C NMR spectrum of 3:1 S:MetHCl

S15 The absorption (dashed) and emission (solid) spectra for compound 4b

S16 The absorption (dashed) and emission (solid) spectra for compound 4c

S17 The absorption (dashed) and emission (solid) spectra for compound 4d

S18 The absorption (dashed) and emission (solid) spectra for compound 4e

S19 The absorption (dashed) and emission (solid) spectra for compound 4f

S20 The absorption (dashed) and emission (solid) spectra for compound 4g

S21 The absorption (dashed) and emission (solid) spectra for compound 4h

S22 The absorption (dashed) and emission (solid) spectra for compound 4i