Hierarchical Host-Guest Assemblies Formed on Dodecaborate-Coated Gold Nanoparticles

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1 Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 17 Hierarchical Host-Guest Assemblies Formed on Dodecaborate-Coated Gold Nanoparticles Khaleel I. Assaf, a, * Andreas Hennig, a Shu Peng, b Dong-Sheng Guo, b Detlef Gabel, a Werner M. Nau a a Department of Life Sciences and Chemistry, Jacobs University Bremen, Campus Ring 1, 759 Bremen, Germany. b Department of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 371, People's Republic of China Contents 1. Materials and Methods.... Synthesis of BSH-AuNPs Characterization of BSH-AuNPs.... Polycationic Calixarene-Induced AuNP Aggregation Host-Guest Complexation of BSH and CXAch Characterization of the CXAch Assembly on BSH-AuNPs Critical Aggregation Concentration (CAC) of CXACh in the absence and presence of BSH-AuNPs 5. Size and Zeta Potential Response of BSH-AuNPs Before and After Addition of AchE References... 1

2 Intensity/ % 1. Materials and Methods Chemicals were purchased from Sigma-Aldrich (Germany) and used without further purification. CXAch was synthesized according to the published procedure. 1 Di-sodium undecahydro-mercapto-closo-dodecaborate (BSH) was purchased from Boron Biologicals, Inc. UV-vis measurements were performed on a Varian Cary UV-Visible spectrophotometer and fluorescence measurements were done on a Varian Cary Eclipse fluorimeter. DLS and zeta potential measurements were performed on a Malvern Zetasizer Nano ZS instrument. IR spectra were recorded on a Nicolet 17SX-FT/IR spectrometer using KBr pellets.. Synthesis of BSH-AuNPs A 5-mL aqueous solution of 1 mm HAuCl was boiled vigorously under stirring in a roundbottomed flask and 3. mm trisodium citrate (5 ml) were added. The solution was refluxed for 15 minutes resulting in a color change from pale yellow to deep red. The solution was cooled to room temperature while stirring continuously. The capping with disodium undecahydro-mercapto-closo-dodecarborate (BSH) was achieved by adding 3. mm BSH (175 µl) to the pre-formed citrate-aunps (75 ml) under stirring for days at room temperature. The BSH-AuNPs were subsequently concentrated to ml final volume (ca. µm) and washed several times with water to remove citrate and excess BSH by centrifugation. Gold nanoparticle concentrations were determined by using an extinction coefficient of.7 x 1 L mol 1 cm Characterization of BSH-AuNPs 1 1 BSH-AuNPs Diameter/ nm Figure S1. Size distribution of BSH-AuNPs measured by DLS.

3 Free OD OD NHCl NMeCl NaCl KCl CsCl BaCl CoCl CuCl ZnCl BSH free BSH-AuNPs wavenumber /cm wavenumber/ cm wavenumber/ cm 1 Figure S. FT-IR spectra: BSH and BSH-AuNPs. The presence of the distinct B-H infrared stretching band at ca. 9 cm 1 in the FT-IR spectrum of the BSH-NPs indicates that the BSH molecules are bound to the AuNPs. A 5/ mm salt Figure S3. Dependence of the ratio of the absorbance values at 5 and 5 nm of BSH- AuNPs with 1 mm of different monovalent and divalent cations (as chloride salts). mm NaCl mm NaCl after minutes after minutes / nm / nm Figure S. Absorption spectral changes of AuNPs ( nm) at different NaCl concentrations: citrate-stabilized AuNPs and BSH-AuNPs. 3

4 OD OD. Polycationic Calixarene-Induced AuNP Aggregation :. M : M 3: 5 M :.9 M 5: 1.7 M : 3.53 M 7:.57 M /nm A 5/ CX-NH 3 + / M Figure S5. Absorption spectral changes of. nm BSH-AuNPs with varying CXNH 3 + concentrations in water. The inset shows the respective visual color changes. Dependence of the ratio of the absorbance values at 5 and 5 nm. The inset shows the chemical structure of CXNH 3 + (as chloride salt). Upon addition of excess CXNH 3 + the SPR band retained its original position indicating the formation of a higher-generation supramolecular structure, which we assign to the bi-layer assembly :. M : M 3: 9 M : 1. M 5:. M : 5. M 7:.1 M : 1. M A 5/ /nm 1 CX-NMe / M Figure S. Absorption spectral changes of. nm BSH-AuNPs with varying CXNMe concentrations in water. The inset shows the respective visual color changes. Dependence of the ratio of the absorbance values at 5 and 5 nm. The inset shows the chemical structure of CXNMe, which is protonated in aqueous solution. Upon addition of excess CXNMe the SPR band retained its original position indicating the formation of a highergeneration supramolecular structure, which we assign to the bi-layer assembly.

5 Intensity Intensity 5. Host-Guest Complexation of BSH and CXAch / nm K a = 1. 1 M 1 1 BSH/ M Figure S7. Fluorescence displacement titration of 1,-ANS (1 M) complexed to CXAch ( M) by addition of free BSH as a competitive guest. Fitted data by assuming a 1:1 binding model from which the association constant was derived. The initial increase in the fluorescence intensity at low BSH concentration (> M) might be attributed to a ternary complex formation (CXAcH 1,-ANS BSH).. Characterization of the CXAch Assembly on BSH-AuNPs Table S1. Absorption peak position ( ), average diameter (d), and zeta potential ( ) of BSH- AuNPs a at different CXAch concentrations. [CXAch]/µM max / nm d/ nm / mv b a Measurements were done at 5 C with nm BSH-AuNP solutions. b Measured for free CXAch, without AuNP. 7. Critical Aggregation Concentration (CAC) of CXACh in the absence and presence of BSH-AuNPs The CAC value for the CXAch was determined for CXAch in the presence and absence of the NPs by using pyrene as a probe. Figure S shows that, without NPs, CXAch exhibits a CAC of 3.5 µm. With NPs, two steps of aggregation were observed, the first is assigned to the formation of a bilayer on the BSH-AuNP surface at ca. 1.5 µm CXAch and the second to the formation of CXAch micelles/vesicles at ca. 13 µm. 5

6 I 1 /I 3 1. Intensity/ % Intensity/ % I 1 /I CAC = 3.5 M CXACh bilayer at 1.5 M CAC = 13 M CXAch/ M CXAch/ M Figure S. Determination of the CAC values of CXACh in the absence and in the presence of nm BSH-AuNPs by using pyrene ( μm) as a probe in water at ph 7., exc = 33 nm. Different emission slits were used in the two measurements leading to different initial values of I 1 /I 3 for instrumental reasons.. Size and Zeta Potential Response of BSH-AuNPs Before and After Addition of AchE BSH-AuNPs-CXAch (no AchE) zeta potential = +3 mv diameter = 1 nm BSH-AuNPs-CXAch (with AchE) zeta potential = 17 mv diameter = 15 nm size/ d.nm size/ d.nm Figure S9. Size distribution and zeta potential of the BSH-AuNPs-CXAch assembly ( nm BSH-AuNPs and 1.5 μm CXACh): without AchE and with AchE ( U ml 1 ) after hours reaction time. 9. References 1. Z. Xu, S. Peng, Y. Y. Wang, J. K. Zhang, A. I. Lazar and D.-S. Guo, Adv. Mater., 1,, 7.. X. O. Liu, M. Atwater, J. H. Wang and Q. Huo, Colloids Surf., B, 7, 5, 3.

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