Blue-shift of photoluminescence induced by coupling effect of a nanohybrid composed of fluorophore–phenothiazine derivative and gold nanoparticles
Source abstract
Abstract
A flurophore–phenothiazine derivative {2-[(10-ethyl-10H-phenothiazin-3-yl)-methylene] malononitrile, abbreviated as L} is designed, synthesized, and characterized by single crystal X-ray diffraction analysis. Further, L is used to couple with Au NPs to construct L–Au nanohybrid. Upon the coupling effect between L and Au components, blue-shifted photoluminescence with an obvious increased FL lifetime has been achieved. Surface enhanced Raman scattering analysis reveals that L molecules couple with Au NPs through S atoms. The coupling “hot spot” and the energy match between the Femi level of Au NPs and the frontier molecular orbital energy of L are effective factors in distributing the photogenerated electrons at the interface to tune the optical property. A D-π-A type phenothiazine derivative (L) was synthesized and used to prepare nanohybrid with Au NPs. L molecules coupled with Au NPs through S atoms, which brought about significant blue-shift of the fluorescence and an obvious increase of FL lifetime.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanocluster Synthesis and Applications · Advanced biosensing and bioanalysis techniques · Gold and Silver Nanoparticles Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (67)
Show source-provided references
1. Aldeek F, Muhammed MAH, Palui G, Zhan N, Mattoussi H (2013) Growth of highly fluorescent polyethylene glycol- and zwitterion-functionalized gold nanoclusters. ACS Nano 7:2509–251110.1021/nn305856t ↗
2. Babu J, George J, Varma RL (2013) Metal-induced fluorescence lifetime enhancement of quinaldine chromophore on gold nanoparticle surface. New J Chem 37:2426–243210.1039/c3nj00287j ↗
3. Cao F, Deng R, Liu D, Song S, Wang S, Su S, Zhang H (2011) Fabrication of fluorescent silica–Au hybrid nanostructures for targeted imaging of tumor cells. Dalton Trans 40:4800–480210.1039/c1dt10106d ↗
4. Carlos LD, Ferreira RAS, Bermudez VdeZ, Julián-López B, Escribano P (2011) Progress on lanthanide-based organic–inorganic hybrid phosphors. Chem Soc Rev 40:536–54910.1039/C0CS00069H ↗
5. Casanova-Moreno JR, Bizzotto D (2013) What happens to the thiolates created by reductively desorbing SAMs? An in situ study using fluorescence microscopy and electrochemistry. Langmuir 29:2065–207410.1021/la305170c ↗
6. Chen LY, Ou CM, Chen WY, Huang CC, Chang HT (2013) Synthesis of photoluminescent Au ND–PNIPAM hybrid microgel for the detection of Hg2+. ACS Appl Mater Interfaces 5:4383–438810.1021/am400628p ↗
7. Corma A, Garcia H (2008) Supported gold nanoparticles as catalysts for organic reactions. Chem Soc Rev 37:2096–212610.1039/b707314n ↗
8. Costi R, Saunders AE, Elmalem E, Salant A, Banin U (2008) Visible light-induced charge retention and photocatalysis with hybrid CdSe–Au nanodumbbells. Nano Lett 8:637–64110.1021/nl0730514 ↗
9. Das A, Li T, Nobusada K, Zeng Q, Rosi NL, Jin R (2012) Total structure and optical properties of a phosphine/thiolate-protected Au24 nanocluster. J Am Chem Soc 134:20286–2028910.1021/ja3101566 ↗
10. Dulkeith E, Morteani AC, Niedereichholz T, Klar TA, Feldmann J, Levi SA, van Veggel FCJM, Reinhoudt DN, Möller M, Gittins DI (2002) Fluorescence quenching of dye molecules near gold nanoparticles: radiative and nonradiative Effects. Phys Rev Lett 89:20300210.1103/PhysRevLett.89.203002 ↗
11. Durr NJ, Larson T, Smith DK, Korgel BA, Sokolov K, Ben-Yakar A (2007) Two-photon luminescence imaging of cancer cells using molecularly targeted gold nanorods. Nano Lett 7:941–94510.1021/nl062962v ↗
12. Frisch MJGWT, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision B. 01. Gaussian Inc., Wallingford
13. Gorin DJ, Sherry BD, Toste FD (2008) Ligand effects in homogeneous Au catalysis. Chem Rev 108:3351–337810.1021/cr068430g ↗
14. Grosso D, Ribot F, Boissiereab C, Sanchez C (2011) Molecular and supramolecular dynamics of hybrid organic–inorganic interfaces for the rational construction of advanced hybrid nanomaterials. Chem Soc Rev 40:829–84810.1039/C0CS00039F ↗
15. Heimel G, Duhm S, Salzmann I, Gerlach A, Strozecka A, Niederhausen J, Bürker C, Hosokai T, Fernandez-Torrente I, Schulze G, Winkler S, Wilke A, Schlesinger R, Frisch J, Bröker B, Vollmer A, Detlefs B, Pflaum J, Kera S, Franke KJ, Ueno N, Pascual JI, Schreiber F, Koch N (2013) Charged and metallic molecular monolayers through surface-induced aromatic stabilization. Nat Chem 5:187–19410.1038/nchem.1572 ↗
16. Heo JH, Im SH, Noh JH, Mandal TN, Lim HS, Chang JA, Lee YH, Kim H, Sarkar A, Nazeeruddin MK, Grätzel M, Seok SII (2013) Efficient inorganic–organic hybrid heterojunction solar cells containing perovskite compound and polymeric hole conductors. Nat Photonics 7:486–49110.1038/nphoton.2013.80 ↗
17. Hussain I, Graham S, Wang Z, Tan B, Sherrington DC, Rannard SP, Cooper AI, Brust M (2005) Size-controlled synthesis of near-monodisperse gold nanoparticles in the 1–4 nm range using polymeric stabilizers. J Am Chem Soc 127:16398–1639910.1021/ja055321v ↗
18. Jovic V, Chen WT, Sun-Waterhouse D, Blackford MG, Idriss H, Waterhouse GIN (2013) Effect of gold loading and TiO2 support composition on the activity of Au/TiO2 photocatalysts for H2 production from ethanol–water mixtures. J Catalysis 305:307–31710.1016/j.jcat.2013.05.031 ↗
19. Jung HS, Xg Chen, Kim JS, Yoon J (2013) Recent progress in luminescent and colorimetric chemosensors for detection of thiols. Chem Soc Rev 42:6019–603110.1039/c3cs60024f ↗
20. Kamińska I, Opallo M, Łaszcz A, Czerwinski A, Niedziolka-Jonsson J (2013) (Bio)electrocatalysis at tin-doped indium oxide nanoparticulate film decorated with gold. Electrochim Acta 106:165–17110.1016/j.electacta.2013.05.089 ↗
21. Kim GW, Cho MJ, Yu YJ (2007) Red emitting phenothiazine dendrimers encapsulated 2-{2-[2-(4-dimethylaminophenyl)vinyl]-6-methylpyran-4-ylidene}malononitrile derivatives. Chem Mater 19:42–5010.1021/cm0618493 ↗
22. Kim KS, Kim JH, Kim H, Laquai F, Arifin E, Lee JK, Yoo SI, Sohn BH (2012) Switching off FRET in the hybrid assemblies of diblock copolymer micelles, quantum dots, and dyes by plasmonic nanoparticles. ACS Nano 6:5051–505910.1021/nn301893e ↗
23. Kim WJ, Kim S, Kim AR, Yoo DJ (2013) Direct detection system for Escherichia coli using Au–Ag alloy microchips. Ind Eng Chem Res 52:7282–728810.1021/ie3022797 ↗
24. Kimura K, Naya S, Jinnouchi Y, Tada H (2012) TiO2 crystal form-dependence of the Au/TiO2 plasmon photocatalyst’s activity. J Phys Chem C 116:7111–711710.1021/jp301681n ↗
25. Kong L, Yang JX, Hao XP, Zhou HP, Wu JY, Hao FY, Li L, Zhang SY, Jin BK, Tao XT, Jiang MH, Tian YP (2010) Tuning the optical properties of flurophore–hexylcarbazole organic nanoribbons with dispersed inorganic nanocrystals (AgNCs). J Mater Chem 20:7372–737710.1039/c0jm00004c ↗
26. Kong L, Yang JX, Xue ZM, Zhou HP, Cheng LJ, Zhang Q, Wu JY, Jin BK, Zhang SY, Tian YP (2013) Regulation of luminescence band and exploration of antibacterial activity of a nanohybrid composed of fluorophore–phenothiazine nanoribbons dispersed with Ag nanoparticles. J Mater Chem C 1:3047–305710.1039/c3tc90042h ↗
27. Kou J, Bennett-Stamper C, Varma RS (2013) Green synthesis of noble nanometals (Au, Pt, Pd) using glycerol under microwave irradiation conditions. ACS Sustainable Chem Eng 1:810–81610.1021/sc400007p ↗
28. Lebeau B, Innocenzi P (2011) Hybrid materials for optics and photonics. Chem Soc Rev 40:886–90610.1039/c0cs00106f ↗
29. Lim SI, Zhong CJ (2008) Molecularly mediated processing and assembly of nanoparticles: exploring the interparticle interactions and structures. Acc Chem Res 42:798–80810.1021/ar8002688 ↗
30. Lim SI, Zhong CJ (2009) Molecularly mediated processing and assembly of nanoparticles: exploring the interparticle interactions and structures. Acc Chem Res 42:798–80810.1021/ar8002688 ↗
31. Lin SY, Zhu WQ, Jin YH, Crozier KB (2013) Surface-enhanced Raman scattering with Ag nanoparticles optically trapped by a photonic crystal cavity. Nano Lett 13:559–56310.1021/nl304069n ↗
32. Liu WL, Lin FC, Yang YC, Huang CH, Gwo S, Huang MH, Huang JS (2013) The influence of shell thickness of Au at TiO2 core–shell nanoparticles on the plasmonic enhancement effect in dye-sensitized solar cells. Nanoscale 5:7953–796210.1039/c3nr02800c ↗
33. López-López M, Ferrando JL, García-Ruiz C (2013) Dynamite analysis by Raman spectroscopy as a unique analytical tool. Anal Chem 85:2595–260010.1021/ac302774w ↗
34. Mehdi A, Reye C, Corriu R (2011) From molecular chemistry to hybrid nanomaterials: design and functionalization. Chem Soc Rev 40:563–57410.1039/B920516K ↗
35. Mehta VN, Kumar MA, Kailasa SK (2013) Colorimetric detection of copper in water samples using dopamine dithiocarbamate-functionalized Au nanoparticles. Ind Eng Chem Res 52:4414–442010.1021/ie302651f ↗
36. Mizoshita N, Taniab T, Inagaki S (2011) Syntheses, properties and applications of periodic mesoporous organosilicas prepared from bridged organosilane precursors. Chem Soc Rev 40:789–80010.1039/C0CS00010H ↗
37. Murphy CJ, Gole AM, Stone JW, Sisco PN, Alkilany AM, Goldsmith EC, Baxter SC (2008) Gold nanoparticles in biology: beyond toxicity to cellular imaging. Acc Chem Res 41:1721–173010.1021/ar800035u ↗
38. Nakamoto K (1978) Infrared and Raman spectra of inorganic and coordination compounds. Wiley, New York, p 350
39. Nambiar SR, Aneesh PK, Rao TP (2013) Ultrasensitive voltammetric determination of catechol at a gold atomic cluster/poly(3,4-ethylenedioxythiophene) nanocomposite electrode. Analyst 138:5031–503810.1039/c3an00518f ↗
40. Nerngchamnong N, Yuan L, Qi DC, Li J, Thompson D, Nijhuis CA (2013) The role of van der Waals forces in the performance of molecular diodes. Nature Nanotechnol 8:113–11810.1038/nnano.2012.238 ↗
41. Nikoobakht B, El-Sayed MA (2003) Preparation and growth mechanism of gold nanorods (NRs) using seed-mediated growth method. Chem Mater 15:1957–196210.1021/cm020732l ↗
42. Peng S, Zheng Q, Zhang X, Dai L, Zhu J, Pi Y, Hu X, Cheng W, Zhou C, Sha Y, Ao Y (2013) Detection of ADAMTS-4 activity using a fluorogenic peptide-conjugated Au nanoparticle probe in human knee synovial fluid. ACS Appl Mater Interfaces 5:6089–609610.1021/am400854z ↗
43. Shang L, Dörlich RM, Brandholt S, Schneider R, Trouillet V, Bruns M, Gerthsen D, Nienhau GU (2011) Facile preparation of water-soluble fluorescent gold nanoclusters for cellular imaging applications. Nanoscale 3:2009–201410.1039/c0nr00947d ↗
44. Sheldrick GM (1997) SHELXTL V5.1 software reference manual. Bruker, AXS Inc, Madison
45. Shi L, Wang A, Zhang T, Zhang B, Su D, Li H, Song Y (2013) One-step synthesis of Au–Pd alloy nanodendrites and their catalytic activity. J Phys Chem C 117:12526–1253610.1021/jp4013202 ↗
46. Singh MP, Strouse GF (2010) Involvement of the LSPR spectral overlap for energy transfer between a dye and Au nanoparticle. J Am Chem Soc 132:9383–939110.1021/ja1022128 ↗
47. Sk MP, Jana CK, Chattopadhyay A (2013) A gold–carbon nanoparticle composite as an efficient catalyst for homocoupling reaction. Chem Commun 49:8235–823710.1039/c3cc43726d ↗
48. Sperling RA, Gil PR, Zhang F, Zanella M, Parak WJ (2008) Biological applications of gold nanoparticles. Chem Soc Rev 37:1896–190810.1039/b712170a ↗
49. Sun WF, Zhang BG, Li YJ, Pritchett TM, Li ZJ, Haley JE (2010) Broadband nonlinear absorbing platinum 2,2′-bipyridine complex bearing 2-(benzothiazol-2′-yl)-9,9-diethyl-7-ethynylfluorene ligands. Chem Mater 22:6384–639210.1021/cm102494j ↗
50. Syed LU, Swisher LZ, Huff H, Rochford C, Wang F, Liu J, Wu J, Richter M, Balivada S, Troyer D, Li J (2013) Luminol-labeled gold nanoparticles for ultrasensitive chemiluminescence-based chemical analyses. Analyst 138:5600–560910.1039/c3an01005h ↗
51. Tanabe KK, Cohen SM (2011) Postsynthetic modification of metal–organic frameworks—a progress report. Chem Soc Rev 40:498–51910.1039/C0CS00031K ↗
52. Tran-Thi TH, Dagnelie R, Crunaire S, Nicole L (2011) Optical chemical sensors based on hybrid organic–inorganic sol–gel nanoreactors. Chem Soc Rev 40:621–63910.1039/C0CS00021C ↗
53. Wang XC, Tian YP, Kan YH, Zuo CY, Wu JY, Jin BK, Zhou HP, Yang JX, Zhang SY, Tao XT, Jiang MH (2009) Functionalized ferrocenes and ferroceniums: synthesis, crystal structures and electrochemical properties based on carbazole/phenothiazine-ferrocene conjugated molecules. Dalton Trans. doi: 10.1039/B900705A
54. Wang T, Zhang X, Pan Y, Miao X, Su Z, Wang C, Li X (2011) Fabrication of doxorubicin functionalized gold nanorod probes for combined cancer imaging and drug delivery. Dalton Trans 40:9789–979410.1039/c1dt10565e ↗
55. Wang J, Lee YJ, Chadha AS, Yi J, Jespersen ML, Kelley JJ, Nguyen HM, Nimmo M, Malko AV, Vaia RA, Zhou W, Hsu JWP (2013a) Effect of plasmonic Au nanoparticles on inverted organic solar cell performance. J Phys Chem C 117:85–9110.1021/jp309415u ↗
56. Wang F, Liu X, Lu CH, Willner I (2013b) Cysteine-mediated aggregation of Au nanoparticles: the development of a H2O2 sensor and oxidase-based biosensors. ACS Nano 7:7278–728610.1021/nn402810x ↗
57. Wilson R (2008) The use of gold nanoparticles in diagnostics and detection. Chem Soc Rev 37:2028–204510.1039/b712179m ↗
58. Yang J, Elim HI, Zhang QB, Lee JY, Ji W (2006) Rational synthesis, self-assembly, and optical properties of PbS–Au heterogeneous nanostructures via preferential deposition. J Am Chem Soc 128:11921–1192610.1021/ja062494r ↗
59. Yu SY, Sun QF, Lee TK, Cheng ECC, Li YZ, Yam VWW (2008) Au36 crown: a macrocyclization directed by metal–metal bonding interactions. Angew Chem Int Ed 47:4551–455410.1002/anie.200801001 ↗
60. Yuan J, Xu Y, Müller AHE (2011) One-dimensional magnetic inorganic–organic hybrid nanomaterials. Chem Soc Rev 40:640–65510.1039/c0cs00087f ↗
61. Zeng C, Li T, Das A, Rosi NL, Jin R (2013) Chiral structure of thiolate-protected 28-gold-atom Nanocluster determined by X-ray crystallography. J Am Chem Soc 135:10011–1001310.1021/ja404058q ↗
62. Zhang X, Xie Y, Yu W, Zhao Q, Jiang MH, Tian YP (2003) Formation of a novel 1D supramolecule [HgCl2(ptz)]2·HgCl2 (ptz = phenothiazine): a new precursor to submicrometer Hg2Cl2 rods. Inorg Chem 42:3734–373710.1021/ic034055o ↗
63. Zhang Y, Li L, Yang H, Ding Y, Su M, Zhu J, Yan M, Yu J, Song X (2013a) Gold–silver nanocomposite-functionalized graphene sensing platform for an electrochemiluminescent immunoassay of a tumor marker. RSC Adv 3:14701–1470910.1039/c3ra41666f ↗
64. Zhang H, Watanabe T, Okumura M, Haruta M, Toshima N (2013b) Crown Jewel catalyst: how neighboring atoms affect the catalytic activity of top Au atoms? J Catal 305:7–1810.1016/j.jcat.2013.04.012 ↗
65. Zhao Y, Pérez-Segarra W, Shi Q, Wei A (2005) Dithiocarbamate assembly on gold. J Am Chem Soc 127:7328–732910.1021/ja050432f ↗
66. Zhou H, Zhang YY, Liu J, Xu JJ, Chen HY (2012) Electrochemiluminescence resonance energy transfer between CdS:EU nanocrystals and Au nanorods for sensitive DNA detection. J Phys Chem C 116:17773–1778010.1021/jp305076g ↗
67. Zhu H, Du ML, Zou ML, Xu CS, Fu YQ (2012) Green synthesis of Au nanoparticles immobilized on halloysite nanotubes for surface-enhanced Raman scattering substrates. Dalton Trans 41:10465–1047110.1039/c2dt30998j ↗