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Supplementary Information

Structural insight into the photoinduced E→Z isomerisation of cinnamate embedded in ZnAl and MgAl layered double hydroxides

Zita Timár

a,b

, Gábor Varga

a,b

, Márton Szabados

a,b

, Krisztián Csankó

c

, Tünde Alapi

d

, Claude Forano

e

, Vanessa Prevot

e

, Pál Sipos

b,d

, István Pálinkó

a,b*

aDepartment of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720,Hungary

bMaterials and Solution Structure Research Group and Interdisciplinary Excellence Centre, Institute of Chemistry, University of Szeged, Aradi Vértanúk tere 1, Szeged, H-6720, Hungary

cBiological Research Centre, Temesvári krt. 62, Szeged, H-6726, Hungary

dDepartment of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, Szeged, H-6720, Hungary

eUniversité Clermont Auvergne, CNRS, SIGMA Clermont, ICCF, F-63000 Clermont-Ferrand, France

To whom correspondence should be addressed.

E-mail: palinko@chem.u-szeged.hu (I. Pálinkó)

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Table S1

The determined cell parameters and interlayer distances of the pristine LDH and the composites as well as the differences in asymmetric and symmetric vibrations of the carboxylate groups of the interlayered cinnamate isomers.

LDH composites a (Å) c (Å) Interlayer distance (Å)

(as(COO–)-

s(COO-)) (cm–1)

Mg2Al-NO3 3.0 31.5 8.7

Mg2Al-E-Cin 3.0 58.1 17.7 143

Mg2Al-Z-Cin 3.0 68.7 21.3 187

Mg2Al-E-Cin (slurry, after

irradiation) 3.0 58.8 18.1 160

Zn2Al-NO3 3.06 26.58 8.86

Zn2Al-E-Cin 3.05 53.14 17.71 143

Zn2Al-Z-Cin 3.04 62.63 20.88 162

Zn2Al-E-Cin (slurry, after

irradiation) 3.0 57.9 17.7 160

Table S2

FT-IR data of Na-E-Cin, Na-Z-Cin, Mg2Al-E-Cin, Mg2Al-Z-Cin, Mg2Al-NO3 LDHs;

assignments are according to ref. [39].

Infrared vibration band (cm-1)

Na-E-Cin Mg2Al-E-Cin Na-Z-Cin Mg2Al-Z-Cin Mg2Al-NO3 Assignment by ref. [39]

608 623 (OMg,AlO)

635 623 631 706 (OMg,AlO)

690 686 690 683 (CCC)

721 717 710 (CCC)+(CH)ar

773 777 758 764 (CH)ar+(HCCO)+(OC

OC)

799 791 795 (Mg,AlO6)

830 (Mg,AlOH)

849 850 856 856 s(COO-)+(CH)cinn

878 880 882 883 (CH)ar

932 941

972 978 968 (CCH)cinn

1005 1007 (CCC)+ (CCC)

1032 1032 (CH)ar+ (CC)ar

1074 1070 1074 1076 (CH)ar+ (CC)ar

1182 1184 (CH)ar+ (CC)ar

1211 1211

1244 1248 (CH)cinn

1294 1290 1356 (CH)cinn+ (CC)

1357 1363 s(COO-)

1386 1388 1386 (CH)ar+ (CH)cinn

1413 1394 s(COO-)

1450 1450 (CH)+ (CC)ar

1498 1499 1491 1493 (CH)+ (CC)ar

1546 1537 1562 1550 as(COO-)

1576 1595 (CC)ar+ (CH)+ (CCC)

1639 1637 1647 1637 1643 (C=C)cinn

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Fig. S1. Molecular structures of E-Cin and Z-Cin.

1800 1600 1400 1200 1000 800 600

D E

C

B 1388 1359

1633 1545

1396 16391533

1357 15951386

1647

1546 1413 1639

603 1384

Kubelka-Munk

Wavenumber (cm–1)

1635 A

Fig. S2. IR spectra of the A: pristine Zn2Al-LDH, B: sodium E-cinnamate, C: sodium Z- cinnamate, D: Zn2Al-E-Cin LDH, E: Zn2Al-Z-Cin LDH.

5.1 Å

1 2 3 1’

2’

3’ 4’

5’

6’

1 2 1’ 3 3’ 2’

4’

5’ 6’ 7.9 Å

Z-Cin E-Cin

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Fig. S3 (A) X-ray diffractograms and (B) IR spectra of a) Zn2Al-E-Cin LDH, b) Zn2Al-Z-Cin LDH, c) Zn2Al-E-Cin LDH (solid state) irradiated at 254 nm for 2 h, d) Zn2Al-E-Cin LDH (slurry phase – suspended in methanol) irradiated at 254 nm for 2 h.

240 260 280 300 320 340 360

Absorbance (a.u.)

Wavelenght (nm) A —

B —

C —

D —

—

F —

269 nm

Fig. S4. UV-Vis spectra of the supernatants of the mixture of sodium E-cinnamate and Mg2Al LDH, A: before irradiation, after various irradiation times, B: 1 h, C: 2 h, D: 3 h, E: 4 h and F:

24 h.

1800 1600 1400 1200 1000 800 600

1535 1396 1637

1535 1394 1635

1388 1359

16331545

1533 1396

Kubelka-Munk

Wavenumber (cm-1)

1641

10 20 30 40 50 60

009

009 006

006 003

003

012

012

110

110

012 110 006009

003

012 110 009

006

Intensity (a.u.)

2Q (°)

003

d)

c)

b)

a)

(A)

d)

c)

b)

a)

(B)

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240 260 280 300 320 340 360

Absorbance (a.u.)

Wavelenght (nm) A —

B —

C —

D —

—

F —

269 nm

Fig. S5. UV-Vis spectra of the supernatants of the mixture of sodium E-cinnamate and Zn2Al LDH A: before the irradiation, after various irradiation times B: 1 h, C: 2 h, D: 3 h, E: 4 h and F: 24 h.

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240 260 280 300 320 340 360

B

Absorbance (a.u.)

Wavelength (nm) E

A C D

269 → 264 → 259 → 259 → 259

Fig. S6. UV-Vis spectra of the supernatants of ZnAl-E-Cin LDH A: before irradiation, after irradiation for B: 1 h, C: 2 h, D: 3 h and E: 4 h.

Ábra

Fig. S1. Molecular structures of E-Cin and Z-Cin.
Fig. S3 (A) X-ray diffractograms and (B) IR spectra of a) Zn 2 Al-E-Cin LDH, b) Zn 2 Al-Z-Cin LDH, c) Zn 2 Al-E-Cin LDH (solid state) irradiated at 254 nm for 2 h, d) Zn 2 Al-E-Cin LDH (slurry phase – suspended in methanol) irradiated at 2
Fig. S5. UV-Vis spectra of the supernatants of the mixture of sodium E-cinnamate and Zn 2 Al LDH A: before the irradiation, after various irradiation times B: 1 h, C: 2 h, D: 3 h, E: 4 h and F: 24 h
Fig. S6. UV-Vis spectra of the supernatants of ZnAl-E-Cin LDH A: before irradiation, after irradiation for B: 1 h, C: 2 h, D: 3 h and E: 4 h

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