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1 Luminescent Alkynyl-Gold(I) Coumarin Derivatives and Their Biological Activity Julià Arcau, a Vincent Andermark, b Elisabet Aguiló, a,c Albert Gandioso, a Artur Moro, d Mario Cetina, c# João Carlos Lima, d Kari Rissanen, c Ingo tt, b Laura Rodríguez a,* a Departament de Química Inorgànica, Universitat de Barcelona, Barcelona, Spain. Fax: ; Tel.: laura.rodriguez@qi.ub.es. b Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig, Beethovenstr. 55, 806 Braunschweig. c Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.. Box 5, 00 Jyväskylä, Finland. d REQUIMTE, Departamento de Química, CQFB, Universidade Nova de Lisboa, Monte de Caparica, Portugal. #Present address: Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 8a, HR-0000 Zagreb, Croatia. Supplementary Material S

2 7 H5 H6 6 5 H H7 H H H Figure S H-NMR spectrum of compound in CDCl (s) 5.5 J (s) 6 C (s) 65 H (s).88 (s) (s) 87. B (s) 65 F (s) 5.76 G (s). (s) 0. (s) (s) (s) 8.8 D (s) 55. I (s) Figure S. C-NMR spectrum of compound in CDCl. S

3 x0 +ESI Scan (00-98 min, 7 scans) Frag=75.0V MSD77d Subtract ().... [M + H] Counts vs. Mass-to-Charge (m/z) Figure S. ESI-MS(+) spectrum of compound. Figure S. Molecular structure for. S

4 Figure S5. Crystal packing along the b axis (left) and view of the six hydrogen bonds that connect the molecules of in the crystal (right). Reference molecule is shown in black color. Figure S6. Crystal packing of along a axis. S

5 PPh + Figure S7. H-NMR spectrum of a in CDCl AuPPC7 [article: a] Figure S8. C-NMR spectrum of a in CDCl. S5

6 x0 -ESI Scan (8 min) Frag=75.0V MSD5.d Subtract () (595,059) Counts vs. Mass-to-Charge (m/z) Figure S9. ESI-MS(+) spectrum of compound a. Figure S Crystal packing of a along the b axis. Insert: π π interaction between two anionic units of a. S6

7 . H C9 N P Au N N H N-CH-N H C5 H C8 H C H C H N-CH-P H C Figure S H-NMR spectrum of b in CDCl. Figure S. C-NMR spectrum of b in CDCl. S7

8 0 N Au P H C9 N N H C5 H C8 H C H C0 H C Figure S. H-NMR spectrum of c in CDCl Figure S. C-NMR spectrum of c in CDCl. S8

9 .0x0 5x0 0x0 ε (M - cm - ) 5.0x Wavelength (nm) Figure S5. Absorption spectra of - in methanol at ca. x0-5 M concentration. x0 6 I (a.u.) x Wavelength (nm) Figure S6. Emission spectra of -. λ exc = 9 nm for and 0 nm for and. S9

10 8.0x0 6 I (a.u.).0x Wavelength (nm) Figure S7. Emission spectra of - recorded at 77K. λ exc = 9 nm for and 0 nm for and..0x0 6 a a a I (a.u.).0x Wavelength (nm) Figure S8. Emission spectra of -a recorded at 77K. λ exc = 9 nm for a and 0 nm for a and a. S0

11 I (a.u.) 6.0x0 6.0x0 6.0x0 6 b b b c c c Wavelength (nm) Figure S9. Emission spectra of -b/c recorded at 77K. λ exc = 9 nm for b/c and 0 nm for b/c and b/c. S

12 Table S X-ray crystallographic data for and a. a Empirical Formula C H 8 C 8 H Au 6 P Molecular Weight (g/mol) Temperature (K) 70 Wavelength (Å) Å Crystal System, space group Monoclínic, P /c (No. ) triclinic, P (No. ) a (Å) 7.0() 5() b (Å) 6.967().8050() c (Å) 6568(6).77() α (º) () β (º) 90() 0.69() γ (º) () V (Å ) 95.05(6) 88.8(9) Z, D calcld (g cm ), 07, 69 Absorption coefficient (mm - ) F(000) 6 98 Crystal size (mm) 9 x 9 x 06 6 x x θ range for data collection [ ].9 to 5.5. to 67.0 Index ranges -6 h 8 - h -7 k -5 k -7 l 5-6 l 7 Collected reflections No Independent reflections No. / R Int. 75 / / 0 Reflections No. I σ(i) 657 Refinement method full-matrix least-squares on F full-matrix least-squares on F Data/restraints/parameters 75 / 0 / / 0 / 505 Goodness-of-fit on F 0 07 Final R indices [I >σ(i)] R = 05, wr = 5 R = 0, wr = 060 R indices (all data) R = 05, wr = 7 R = 06, wr = 060 Largest diff. peak and hole (eå ) 69< ρ< 7 076< ρ< 99 S

13 Table S. Selected bond lengths [Å] and angles [ ] of. Distance (Å) Angle ( º ) -C 8() -C-C 7.06(8) -C9 78() -C- 6.0(9) -C () -C-C 6.9(8) C-C () C--C9 70(6) C-C 7() C-C-C0 70(9) C-C0 5() C7--C 7.77(5) -C7 7() C-C-C 77.6() C-C 66() C-C 80() Table S. Selected bond lengths [Å] and angles [ ] for a. Distance (Å) Distance (Å) Angle ( º ) Angle ( º ) Au-C.00() Au-C.007() C-Au-C 78.7() C-C5-C6 77.5() -C 90() -C6 () C-C-C 76.9() C5-C6-08.5() -C 09() 5-C7 8() -C-C.() C6--C 6.9() -C () 6-C7 05() C7--C 8.0() C-C () C-C5 78(5) C-C 70() C5-C6 6() C-C 88() C8-C9 8(5) S

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