Arylazoimidazole complexes of lead(ii)-halide and their photochromism
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1 1 Electronic Supplementary Data Arylazoimidazole complexes of lead(ii)-halide and their photochromism Debashis Mallick a, Bharati Chowdhury b, Chandana Sen b, Kamal Krishna Sarkar c, Srikanta Jana b, Sudipa Mondal b & Chittaranjan Sinha b, * a Department of Chemistry, Mrinalini Datta Mahavidyapith, Birati, Kolkata , India b Department of Chemistry, Inorganic Chemistry Section, Jadavpur University, Kolkata , India c Department of Chemistry, Mahadevananda Mahavidyalaya, SN Banerjee Rd, Monirampore, Kolkata, West Bengal , India crsjuchem@gmail.com No. Contents Pg No. 1 Fig. S1 1 H NMR spectrum of Meaai-C 6 H Fig. S2 1 H NMR spectrum of Meaai-C 8 H Fig. S3 1 H NMR spectrum of [Pb(Meaai-C 6 H 13 )I 2 ] n 3 4 Fig. S4 HRMS spectrum of [Pb(Meaai-C 6 H 13 )I 2 ] n (11b) 3 5 Fig. S5 Spectral changes of Meaai-C 6 H 13 (2b) in MeOH upon repeated irradiation at 364 nm at 3 min interval at 25 0 C 6 Fig. S6 Photochromism of Meaai-C 6 H 13 (2b) in toluene and resistance to repeated irradiation upon UV light irradiation at 362 nm for 10 min followed by irradiation of visible light at 455 nm for 10 min 7 Fig. S7 The Eyring plots of rate constants of E-to Z thermal isomerisation of [Pb(Meaai-C 6 H 13 ) I) 2 ] (11b) at different temperatures Fig. S8 FMOs of complexes 5b, 8b and 11b 5 9 Fig. S9 FMOs of 11b considering cleavage of Pb-N(azo) bond upon irradiation of UV light and the formation of three coordinated Pb(II)-motif 6 10 Table S1 1 H NMR spectral data in DMSO-d 6 at room temperature 7 11 Table S2 Results of photochromism, rate of conversion and quantum yields upon UV light irradiation of Raai-C n H 2n+1 in methanol at 298 K 12 Table S3 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )Cl 2 ] (5b) 8 13 Table S4 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )Cl 2 ] (5b) 8 14 Table S5 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )Br 2 ] (8b) 9 15 Table S6 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )Br 2 ] (8b) 9 16 Table S7 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )I 2 ] (11b) Table S8 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )I 2 ] (11b) Table S9 Frontier MOs, their energy and composition of three cordinated [Pb(Meaai-C 6 H 13 )I 2 ] (11b) Table S10 Calculated spectral transitions of three cordinated [Pb(Meaai-C 6 H 13 )I 2 ] (11b) 11
2 2 Fig. S1 1 H NMR spectrum of Meaai-C 6 H 13 Fig. S2 1 H NMR spectrum of Meaai-C 8 H 17
3 3 Fig. S3 1 H NMR spectrum of [Pb(Meaai-C 6 H 13 )I 2 ] n Fig. S4 HRMS spectrum of [Pb(Meaai-C 6 H 13 )I 2 ] n (11b)
4 Trans-isomer 1.0 Decreasing Absorbance 0.8 cis-isomer nm Absorbance nm 433 nm 0.2 Isobestic point Wavelength(nm) nm Increasing Isobestic point Wavelength(nm) Fig. S5 Spectral changes of Meaai-C 6 H 13 (2b) in MeOH upon repeated irradiation at 364 nm at 3 min interval at 25 0 C Fig. S6 Photochromism of Meaai-C 6 H 13 (2b) in toluene and resistance to repeated irradiation upon UV light irradiation at 362 nm for 10 min followed by irradiation of visible light at 455 nm for 10 min LnK/T x x x x x10-3 1/T Fig. S7 The Eyring plots of rate constants of E-to Z thermal isomerisation of [Pb(Meaai-C 6 H 13 ) I) 2 ] (11b) at different temperatures
5 5 5b 8b 11b LUMO+2 E-0.55 (Pb,22%;Cl,3%;L,75%) E-0.73eV (Pb,45%;Br,10%,L,45%) E-1.01eV(Pb,34%;I,9%,L,57%) LUMO+1 E (Pb,1%;Cl,0%;L,98%) E-1.03eV(Pb,3%;Br,1%,L,96%) E-1.12eV (Pb,31%;I,9%,L,60%) LUMO E-3.45eV(Pb,1%;Cl,1%,L,98%) E-3.55eV(Pb,0%;Br,2%,L,98%) E-3.64eV(Pb,0%;I,2%,L,97%) HOMO E-6.17eV(Pb,19%;Cl,74%;L,7%) E-5.94eV(Pb,12%;Br,84%,L,4%) E-5.65eV(Pb,4%;I,94%,L,1%) HOMO-1 E-6.46eV(Pb,2%;Cl,97%;L,2%) E-6.07eV(Pb,2%;Br,97%,L,1%) E-5.75eV(Pb,6%;I,93%,L,2%) HOMO-2 E ev(pb,0%;cl,94%;l,5%) E-6.22eV(Pb,0%;Br,98%,L,2%) E-5.87eV(Pb,0%;I,98%,L,2%) Fig. S8 FMOs of complexes 5b, 8b and 11b
6 6 LUMO+2, E = ev,, Pb, 28%, MeaaiC 6 H 13, 64%, I, 8% LUMO+1, E = ev,, Pb:37%, MeaaiC 6 H 13, 53%, I, 10%. LUMO, E = ev; MeaaiC 6 H 13, 98%, I, 2% HOMO, E: ev,, Pb:4%, MeaaiC 6 H 13, 1%; I, 95% HOMO-1; E: ev,, Pb, 6 %; MeaaiC 6 H 13, 2%; I, 92%. HOMO-2,E: ev, Pb:1%; MeaaiC 6 H 13, 2%; I, 98%. Fig. S9 FMOs of 11b considering cleavage of Pb-N(azo) bond upon irradiation of UV light and the formation of three coordinated Pb(II)-motif
7 7 Table S1 1 H NMR spectral data in DMSO-d 6 at room temperature Compounds 4-H s 5-H s 7,11-H d 8,10-H d 9-R s 12-CH 2 t CH 3 t CH 3 - (CH 2 )* -CH 2- bs [Pb(Haai-C 4 H 9 )Cl 2 ](4a) (8.4) [Pb(Meaai-C 4 H 9 )Cl 2 ] (4b) (7.4) (7.1) [Pb(Haai-C 6 H 13 )Cl 2 ] (5a) (8.3) (6.4) [Pb(Meaai-C 6 H 13 )Cl 2 ] (5b) (7.5) (7.0) [Pb(Meaai-C 8 H 17 )Cl 2 ] (6a) (7.8) [Pb(Haai-C 8 H 17 )Cl 2 ] (6b) (7.7) (7.1) [Pb(Haai-C 4 H 9 )Br 2 ] (7a) (8.5) [Pb(Meaai-C 4 H 9 )Br 2 ] (7b) (7.4) (7.0) [Pb(Haai-C 6 H 13 )Br 2 ] (8a) (8.3) (6.4) [Pb(Meaai-C 6 H 13 )Br 2 ] (8b) (7.4) (7.01) [Pb(Meaai-C 8 H 17 )Br 2 ] (9a) (7.8) [Pb(Haai-C 8 H 17 )Br 2 ] (9b) (7.7) (7.3) [Pb(Haai-C 4 H 9 )I 2 ] n (10a) (8.3) [Pb(Meaai-C 4 H 9 )I 2 ] (10b) (7.4) (7.0) [Pb(Haai-C 6 H 13 )I 2 ] (11a) (8.2) (6.4) [Pb(Meaai-C 6 H 13 )I 2 ] (11b) (7.4) (7.0) [Pb(Heaai-C 8 H 17 )I 2 ] (12b) (7.8) [Pb(Meaai-C 8 H 17 )I 2 ] (12b) (7.6) (7.1) s Singlet; d Doublet; t Triplet; bs Broad Singlet; last -CH 3 of respective N-alkyl group (6.4) (6.1) Table S2 Results of photochromism, rate of conversion and quantum yields upon UV light irradiation of Raai-C n H 2n+1 in methanol at 298 K Compds λ π,π* (nm) Isobestic point (nm) Rate of E Z conversion x 10 9 (s -1 ) φ E Z conversion x a , ± b , ± a , ± b , ± a , ± b , ± 0.002
8 8 Table S3 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )Cl 2 ] (5b) Orbital Energy(eV) Composition(%) Pb Chloride ligand LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO Table S4 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )Cl 2 ] (5b) E excitation (ev) λ excitation (nm) Oscillator Key transition Character strength (f) (64%)HOMO-1 LUMO XLCT (66%)HOMO LUMO XLCT, MLCT (60%)HOMO-2 LUMO XLCT (56%)HOMO-4 LUMO ILCT, XLCT (95%)HOMO-9 LUMO ILCT (83%)HOMO LUMO+1 XLCT, MLCT
9 9 Table S5 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )Br 2 ] (8b) Orbital Energy(eV) Composition Pb Bromide ligand LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO Table S6 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )Br 2 ] (8b) E excitation (ev) λ excitation (nm) Oscillator Key transition Character strength (f) (28%)HOMO-2 LUMO XLCT (52%)HOMO LUMO XLCT, MLCT (81%)HOMO-3 LUMO XLCT (49%)HOMO-9 LUMO ILCT (64%)HOMO-1 LUMO+1 XLCT
10 10 Table S7 Frontier MOs, their energy and composition of [Pb(Meaai-C 6 H 13 )I 2 ] (11b) Orbital Energy(eV) Composition Pb Iodide ligand LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO Table S8 Calculated spectral transitions of [Pb(Meaai-C 6 H 13 )I 2 ] (11b) E excitation (ev) λ excitation (nm) Oscillator Key transition Character strength (f) (59%)HOMO-3 LUMO XLCT (80%)HOMO-2 LUMO XLCT (96%)HOMO-7 LUMO ILCT (84%)HOMO-9 LUMO ILCT (68%)HOMO-10 LUMO ILCT (42%)HOMO LUMO+3 XMCT N.B: Metal to ligand charge transfer(mlct); Ligand to metal charge transfer(lmct); Intra ligand charge transfer(ilct); Halide(X) to metal charge transfer(xmct); Halide(X) to ligand charge transfer(xlct)
11 11 Table S9 Frontier MOs, their energy and composition of three cordinated [Pb(Meaai-C 6 H 13 )I 2 ] (11b) Orbital Energy(eV) Composition Pb Iodide ligand LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO LUMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO HOMO Table S10 Calculated spectral transitions of three cordinated [Pb(Meaai-C 6 H 13 )I 2 ] (11b) E excitation (ev) λ excitation (nm) Oscillator Key transition Character strength (f) (45%)HOMO-6 LUMO XLCT (78%)HOMO-5 LUMO LLCT (49%)HOMO-6 LUMO XLCT (95%)HOMO-7 LUMO LLCT (69%)HOMO LUMO+1 XLCT (43%)HOMO LUMO+3 XMCT N.B: Metal to ligand charge transfer (MLCT); Ligand to metal charge transfer (LMCT); Intra ligand charge transfer (ILCT); Halide (X) to metal charge transfer (XMCT); Halide(X) to ligand charge transfer (XLCT)
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