메뉴 건너뛰기




Volumn 48, Issue 8, 2015, Pages 2230-2241

Supramolecular Oligothiophene Microfibers Spontaneously Assembled on Surfaces or Coassembled with Proteins inside Live Cells

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; PROTEIN; THIOPHENE DERIVATIVE;

EID: 84939493113     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00241     Document Type: Article
Times cited : (52)

References (46)
  • 1
    • 79952121316 scopus 로고    scopus 로고
    • One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics
    • Kim, F. S.; Ren, G.; Jenekhe, S. A. One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics Chem. Mater. 2011, 23, 682-732 10.1021/cm102772x
    • (2011) Chem. Mater. , vol.23 , pp. 682-732
    • Kim, F.S.1    Ren, G.2    Jenekhe, S.A.3
  • 2
    • 84898838289 scopus 로고    scopus 로고
    • Self-Assembly of Intramolecular Charge-Transfer Compounds into Functional Molecular Systems
    • Li, Y.; Liu, T.; Liu, H.; Tian, M. Z.; Li, Y. Self-Assembly of Intramolecular Charge-Transfer Compounds into Functional Molecular Systems Acc. Chem. Res. 2014, 47, 1186-1198l 10.1021/ar400264e
    • (2014) Acc. Chem. Res. , vol.47 , pp. 1186-1198l
    • Li, Y.1    Liu, T.2    Liu, H.3    Tian, M.Z.4    Li, Y.5
  • 3
    • 84892559012 scopus 로고    scopus 로고
    • Charge Transport Over Multiple Length Scales in Supramolecular Fiber Transistors: Single Fiber Versus Ensemble Performance
    • Mativetsky, J. M.; Orgiu, E.; Lieberwirth, I.; Pisula, W.; Samorì, P. Charge Transport Over Multiple Length Scales in Supramolecular Fiber Transistors: Single Fiber Versus Ensemble Performance Adv. Mater. 2014, 26, 430-435 10.1002/adma.201303419
    • (2014) Adv. Mater. , vol.26 , pp. 430-435
    • Mativetsky, J.M.1    Orgiu, E.2    Lieberwirth, I.3    Pisula, W.4    Samorì, P.5
  • 5
    • 18044384227 scopus 로고    scopus 로고
    • About Supramolecular Assemblies of π-Conjugated Systems
    • Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. About Supramolecular Assemblies of π-Conjugated Systems Chem. Rev. 2005, 105, 1491-1546 10.1021/cr030070z
    • (2005) Chem. Rev. , vol.105 , pp. 1491-1546
    • Hoeben, F.J.M.1    Jonkheijm, P.2    Meijer, E.W.3    Schenning, A.P.H.J.4
  • 6
    • 84857319239 scopus 로고    scopus 로고
    • Functional Supramolecular Polymers
    • Aida, T.; Meijer, E. W.; Stupp, S. I. Functional Supramolecular Polymers Science 2012, 335, 813-817 10.1126/science.1205962
    • (2012) Science , vol.335 , pp. 813-817
    • Aida, T.1    Meijer, E.W.2    Stupp, S.I.3
  • 7
    • 84929376911 scopus 로고    scopus 로고
    • Fluorescent thiophene-based materials and their outlook for emissive applications
    • Rasmussen, S. C.; Evenson, S. J.; McCausland, C. B. Fluorescent thiophene-based materials and their outlook for emissive applications Chem. Commun. 2015, 51, 4528-4543 10.1039/C4CC09206F
    • (2015) Chem. Commun. , vol.51 , pp. 4528-4543
    • Rasmussen, S.C.1    Evenson, S.J.2    McCausland, C.B.3
  • 8
    • 84899559117 scopus 로고    scopus 로고
    • Oligothiophene Semiconductors: Synthesis, Characterization, and Applications for Organic Devices
    • Zhang, L.; Colella, N. S.; Cherniawski, B. P.; Mannsfeld, S. C. B.; Briseno, A. L. Oligothiophene Semiconductors: Synthesis, Characterization, and Applications for Organic Devices ACS Appl. Mater. Interfaces 2014, 6, 5327-5343 10.1021/am4060468
    • (2014) ACS Appl. Mater. Interfaces , vol.6 , pp. 5327-5343
    • Zhang, L.1    Colella, N.S.2    Cherniawski, B.P.3    Mannsfeld, S.C.B.4    Briseno, A.L.5
  • 9
    • 66149119364 scopus 로고    scopus 로고
    • Oligothiophene Versus β-Sheet Peptide: Synthesis and Self-Assembly of an Organic Semiconductor-Peptide Hybrid
    • Schillinger, E. K.; Mena-Osteritz, E.; Hentschel, J.; Borner, H. G.; Bauerle, P. Oligothiophene Versus β-Sheet Peptide: Synthesis and Self-Assembly of an Organic Semiconductor-Peptide Hybrid Adv. Mater. 2009, 21, 1562-1567 10.1002/adma.200803110
    • (2009) Adv. Mater. , vol.21 , pp. 1562-1567
    • Schillinger, E.K.1    Mena-Osteritz, E.2    Hentschel, J.3    Borner, H.G.4    Bauerle, P.5
  • 10
    • 78649804126 scopus 로고    scopus 로고
    • Rationally controlled helical organization of a multiple-hydrogen-bonding oligothiophene: guest-induced transition of helical-to-twisted ribbons
    • Yagai, S.; Gushiken, M.; Karatsu, T.; Kitamura, A.; Kikkawa, Y. Rationally controlled helical organization of a multiple-hydrogen-bonding oligothiophene: guest-induced transition of helical-to-twisted ribbons Chem. Commun. 2011, 47, 454-456 10.1039/C0CC02225J
    • (2011) Chem. Commun. , vol.47 , pp. 454-456
    • Yagai, S.1    Gushiken, M.2    Karatsu, T.3    Kitamura, A.4    Kikkawa, Y.5
  • 11
    • 70349270892 scopus 로고    scopus 로고
    • Interconvertible Oligothiophene Nanorods and Nanotapes with HighCharge-Carrier Mobilities
    • Yagai, S.; Kinoshita, T.; Kikkawa, Y.; Karatsu, T.; Kitamura, A.; Honsho, Y.; Seki, S. Interconvertible Oligothiophene Nanorods and Nanotapes with HighCharge-Carrier Mobilities Chem.-Eur. J. 2009, 15, 9320-9324 10.1002/chem.200901336
    • (2009) Chem. - Eur. J. , vol.15 , pp. 9320-9324
    • Yagai, S.1    Kinoshita, T.2    Kikkawa, Y.3    Karatsu, T.4    Kitamura, A.5    Honsho, Y.6    Seki, S.7
  • 12
    • 3342922526 scopus 로고
    • The Deformability of the Thiophene Ring: A Key to the Understanding of the Conformational Properties of Oligo- and Polythiophenes
    • Barbarella, G.; Zambianchi, M.; Bongini, A.; Antolini, L. The Deformability of the Thiophene Ring: A Key to the Understanding of the Conformational Properties of Oligo- and Polythiophenes Adv. Mater. 1993, 5, 834-838 10.1002/adma.19930051110
    • (1993) Adv. Mater. , vol.5 , pp. 834-838
    • Barbarella, G.1    Zambianchi, M.2    Bongini, A.3    Antolini, L.4
  • 13
    • 0037149098 scopus 로고    scopus 로고
    • Conformational Analysis of Oligothiophenes and Oligo(thienyl)furans by Use of a Combined Molecular Dynamics/NMR Spectroscopic Protocol
    • Diaz-Quijada, G. A.; Weinberg, N.; Holdcroft, S.; Pinto, B. M. Conformational Analysis of Oligothiophenes and Oligo(thienyl)furans by Use of a Combined Molecular Dynamics/NMR Spectroscopic Protocol J. Phys. Chem. A 2002, 106, 1277-1285 10.1021/jp011784l
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1277-1285
    • Diaz-Quijada, G.A.1    Weinberg, N.2    Holdcroft, S.3    Pinto, B.M.4
  • 15
    • 0033950182 scopus 로고    scopus 로고
    • Evidence for a Strong Sulfur-Aromatic Interaction Derived from Crystallographic Data
    • Zauhar, R. J.; Colbert, C. L.; Morgan, R. S.; Welsh, W. J. Evidence for a Strong Sulfur-Aromatic Interaction Derived from Crystallographic Data Biopolymers 2000, 53, 233-248 10.1002/(SICI)1097-0282(200003)53:3<233::AID-BIP3>3.0.CO;2-4
    • (2000) Biopolymers , vol.53 , pp. 233-248
    • Zauhar, R.J.1    Colbert, C.L.2    Morgan, R.S.3    Welsh, W.J.4
  • 16
    • 84951337215 scopus 로고
    • The chemistry of hypervalent molecules
    • Musher, J. I. The chemistry of hypervalent molecules Angew. Chem., Int. Ed. Engl. 1969, 8, 54-68 10.1002/anie.196900541
    • (1969) Angew. Chem., Int. Ed. Engl. , vol.8 , pp. 54-68
    • Musher, J.I.1
  • 17
    • 0036838403 scopus 로고    scopus 로고
    • The octet rule and hypervalence: two misunderstood concepts
    • Gillespie, R. J.; Silvi, B. The octet rule and hypervalence: two misunderstood concepts Coord. Chem. Rev. 2002, 233-234, 53-62 10.1016/S0010-8545(02)00102-9
    • (2002) Coord. Chem. Rev. , vol.233-234 , pp. 53-62
    • Gillespie, R.J.1    Silvi, B.2
  • 18
    • 84862996200 scopus 로고    scopus 로고
    • Hypervalent Nonbonded Interactions of a Divalent Sulfur Atom. Implications in Protein Architecture and the Functions
    • Iwaoka, M.; Isozumi, N. Hypervalent Nonbonded Interactions of a Divalent Sulfur Atom. Implications in Protein Architecture and the Functions Molecules 2012, 17, 7266-7283 10.3390/molecules17067266
    • (2012) Molecules , vol.17 , pp. 7266-7283
    • Iwaoka, M.1    Isozumi, N.2
  • 19
    • 84923366689 scopus 로고    scopus 로고
    • Molecular length dictates the nature of charge carriers in single-molecule junctions of oxidized oligothiophenes
    • Dell, E. J.; Capozzi, B.; Xia, J.; Venkataraman, L.; Campos, L. M. Molecular length dictates the nature of charge carriers in single-molecule junctions of oxidized oligothiophenes Nat. Chem. 2015, 7, 209-214 10.1038/nchem.2160
    • (2015) Nat. Chem. , vol.7 , pp. 209-214
    • Dell, E.J.1    Capozzi, B.2    Xia, J.3    Venkataraman, L.4    Campos, L.M.5
  • 21
    • 0035185255 scopus 로고    scopus 로고
    • Rigid-Core Oligothiophene-S,S-dioxides with High Photoluminescence Efficiencies Both in Solution and in the Solid State
    • Barbarella, G.; Favaretto, L.; Sotgiu, G.; Antolini, L.; Gigli, G.; Cingolani, R.; Bongini, A. Rigid-Core Oligothiophene-S,S-dioxides with High Photoluminescence Efficiencies Both in Solution and in the Solid State Chem. Mater. 2001, 13, 4112-4122 10.1021/cm010436t
    • (2001) Chem. Mater. , vol.13 , pp. 4112-4122
    • Barbarella, G.1    Favaretto, L.2    Sotgiu, G.3    Antolini, L.4    Gigli, G.5    Cingolani, R.6    Bongini, A.7
  • 22
    • 0141957552 scopus 로고    scopus 로고
    • Solid-State Supramolecular Organization, Established Directly from Powder Diffraction Data, and Photoluminescence Efficiency of Rigid-Core Oligothiophene-S,S-dioxides
    • Tedesco, E.; Della Sala, F.; Favaretto, L.; Barbarella, G.; Albesa-Jové, D.; Pisignano, D.; Gigli, G.; Cingolani, R.; Harris, K. D. M. Solid-State Supramolecular Organization, Established Directly from Powder Diffraction Data, and Photoluminescence Efficiency of Rigid-Core Oligothiophene-S,S-dioxides J. Am. Chem. Soc. 2003, 125, 12277-12283 10.1021/ja035570o
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12277-12283
    • Tedesco, E.1    Della Sala, F.2    Favaretto, L.3    Barbarella, G.4    Albesa-Jové, D.5    Pisignano, D.6    Gigli, G.7    Cingolani, R.8    Harris, K.D.M.9
  • 23
    • 22044431776 scopus 로고    scopus 로고
    • The versatile thiophene: an overview of recent research on thiophene-based materials
    • Barbarella, G.; Melucci, M.; Sotgiu, G. The versatile thiophene: an overview of recent research on thiophene-based materials Adv. Mater. 2005, 17, 1581-1593 10.1002/adma.200402020
    • (2005) Adv. Mater. , vol.17 , pp. 1581-1593
    • Barbarella, G.1    Melucci, M.2    Sotgiu, G.3
  • 25
    • 80455123878 scopus 로고    scopus 로고
    • Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils
    • Palama, I.; Di Maria, F.; Viola, I.; Fabiano, E.; Gigli, G.; Bettini, C.; Barbarella, G. Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils J. Am. Chem. Soc. 2011, 133, 17777-17785 10.1021/ja2065522
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 17777-17785
    • Palama, I.1    Di Maria, F.2    Viola, I.3    Fabiano, E.4    Gigli, G.5    Bettini, C.6    Barbarella, G.7
  • 26
    • 0003045725 scopus 로고
    • Database Analysis of Crystal-structure-determining Interactions involving Sulphur: Implications for the Design of Organic Metals
    • Desiraju, G. R.; Nalini, V. Database Analysis of Crystal-structure-determining Interactions involving Sulphur: Implications for the Design of Organic Metals J. Mater. Chem. 1991, 1, 201-203 10.1039/jm9910100201
    • (1991) J. Mater. Chem. , vol.1 , pp. 201-203
    • Desiraju, G.R.1    Nalini, V.2
  • 28
    • 84939536642 scopus 로고    scopus 로고
    • Di Maria, F. Unpublished results
    • Di Maria, F. Unpublished results.
  • 33
    • 84856189256 scopus 로고    scopus 로고
    • Oligothiophenes as fluorescent markers for Biological Applications
    • Capobianco, M. L.; Barbarella, G.; Manetto, A. Oligothiophenes as fluorescent markers for Biological Applications Molecules 2012, 17, 910-933 10.3390/molecules17010910
    • (2012) Molecules , vol.17 , pp. 910-933
    • Capobianco, M.L.1    Barbarella, G.2    Manetto, A.3
  • 34
    • 68249150547 scopus 로고    scopus 로고
    • Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells
    • Zambianchi, M.; Di Maria, F.; Cazzato, A.; Gigli, G.; Piacenza, M.; Della Sala, F.; Barbarella, G. Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells J. Am. Chem. Soc. 2009, 131, 10892-10900 10.1021/ja902416s
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 10892-10900
    • Zambianchi, M.1    Di Maria, F.2    Cazzato, A.3    Gigli, G.4    Piacenza, M.5    Della Sala, F.6    Barbarella, G.7
  • 35
    • 84893906369 scopus 로고    scopus 로고
    • Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores
    • Di Maria, F.; Palamà, E.; Baroncini, M.; Barbieri, A.; Bongini, A.; Bizzarri, R.; Gigli, G.; Barbarella, G. Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores Org. Biomol. Chem. 2014, 12, 1603-1610 10.1039/c3ob41982g
    • (2014) Org. Biomol. Chem. , vol.12 , pp. 1603-1610
    • Di Maria, F.1    Palamà, E.2    Baroncini, M.3    Barbieri, A.4    Bongini, A.5    Bizzarri, R.6    Gigli, G.7    Barbarella, G.8
  • 36
    • 84886994918 scopus 로고    scopus 로고
    • Physiological formation of fluorescent and conductive protein microfibers in live fibroblasts upon spontaneous uptake of biocompatible fluorophores
    • Viola, I.; Palamà, I. E.; Coluccia, A. M. L; Biasiucci, M.; Dozza, B.; Lucarelli, E.; Di Maria, F.; Barbarella, G.; Gigli, G. Physiological formation of fluorescent and conductive protein microfibers in live fibroblasts upon spontaneous uptake of biocompatible fluorophores Integr. Biol. 2013, 5, 1057-1066 10.1039/c3ib40064f
    • (2013) Integr. Biol. , vol.5 , pp. 1057-1066
    • Viola, I.1    Palamà, I.E.2    Coluccia, A.M.L.3    Biasiucci, M.4    Dozza, B.5    Lucarelli, E.6    Di Maria, F.7    Barbarella, G.8    Gigli, G.9
  • 37
    • 84915750037 scopus 로고    scopus 로고
    • Biocompatible and biodegradable fluorescent microfibers physiologically secreted by live cells upon spontaneous uptake of thiophene fluorophore
    • Palamà, I. E.; Di Maria, F.; D'Amone, S.; Barbarella, G.; Gigli, G. Biocompatible and biodegradable fluorescent microfibers physiologically secreted by live cells upon spontaneous uptake of thiophene fluorophore J. Mater. Chem. B 2015, 3, 151-158 10.1039/C4TB01562B
    • (2015) J. Mater. Chem. B , vol.3 , pp. 151-158
    • Palamà, I.E.1    Di Maria, F.2    D'Amone, S.3    Barbarella, G.4    Gigli, G.5
  • 38
    • 0022476714 scopus 로고
    • Permeability of Small Nonelectrolytes through Lipid Bilayer Membranes
    • Walter, A.; Gutknecht, J. Permeability of Small Nonelectrolytes through Lipid Bilayer Membranes J. Membr. Biol. 1986, 90, 207-217 10.1007/BF01870127
    • (1986) J. Membr. Biol. , vol.90 , pp. 207-217
    • Walter, A.1    Gutknecht, J.2
  • 40
    • 84865305368 scopus 로고    scopus 로고
    • Atomic structure of the vimentin central α-helical domain and its implications for intermediate filament assembly
    • Chernyatina, A. A.; Nicolet, S.; Aebi, U.; Herrmann, H.; Strelkov, S. V. Atomic structure of the vimentin central α-helical domain and its implications for intermediate filament assembly Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 13620-13625 10.1073/pnas.1206836109
    • (2012) Proc. Natl. Acad. Sci. U. S. A. , vol.109 , pp. 13620-13625
    • Chernyatina, A.A.1    Nicolet, S.2    Aebi, U.3    Herrmann, H.4    Strelkov, S.V.5
  • 41
    • 34248578409 scopus 로고    scopus 로고
    • Dissecting the 3-D structure of vimentin intermediate filaments by cryo-electron tomography
    • Goldie, K. N.; Wedig, T.; Mitra, A. K.; Aebi, U.; Herrmann, H.; Hoenger, A. Dissecting the 3-D structure of vimentin intermediate filaments by cryo-electron tomography J. Struct. Biol. 2007, 158, 378-385 10.1016/j.jsb.2006.12.007
    • (2007) J. Struct. Biol. , vol.158 , pp. 378-385
    • Goldie, K.N.1    Wedig, T.2    Mitra, A.K.3    Aebi, U.4    Herrmann, H.5    Hoenger, A.6
  • 42
    • 84880293236 scopus 로고    scopus 로고
    • Supramolecular Construction of Optoelectronic Biomaterials
    • Tovar, J. D. Supramolecular Construction of Optoelectronic Biomaterials Acc. Chem. Res. 2013, 46, 1527-1537 10.1021/ar3002969
    • (2013) Acc. Chem. Res. , vol.46 , pp. 1527-1537
    • Tovar, J.D.1
  • 43
    • 84891752792 scopus 로고    scopus 로고
    • Multi-Colored Fibers by Self-Assembly of DNA, Histone Proteins, and Cationic Conjugated Polymers
    • Wang, F.; Liu, Z.; Wang, B.; Feng, L.; Liu, L.; Lv, F.; Wang, Y.; Wang, S. Multi-Colored Fibers by Self-Assembly of DNA, Histone Proteins, and Cationic Conjugated Polymers Angew. Chem., Int. Ed. 2014, 53, 424-428 10.1002/anie.201308795
    • (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 424-428
    • Wang, F.1    Liu, Z.2    Wang, B.3    Feng, L.4    Liu, L.5    Lv, F.6    Wang, Y.7    Wang, S.8
  • 44
    • 84889880198 scopus 로고    scopus 로고
    • Fabrication of poly (ε-caprolactone) microfiber scaffolds with varying topography and mechanical properties for stem cell-based tissue engineering Applications
    • Ko, J.; Mohtaram, N. K.; Ahmed, F.; Montgomery, A.; Carlson, M.; Lee, P. C. D.; Willerth, S. M.; Jun, M. B. G. Fabrication of poly (ε-caprolactone) microfiber scaffolds with varying topography and mechanical properties for stem cell-based tissue engineering Applications J. Biomater. Sci., Polym. Ed. 2014, 25, 1-17 10.1080/09205063.2013.830913
    • (2014) J. Biomater. Sci., Polym. Ed. , vol.25 , pp. 1-17
    • Ko, J.1    Mohtaram, N.K.2    Ahmed, F.3    Montgomery, A.4    Carlson, M.5    Lee, P.C.D.6    Willerth, S.M.7    Jun, M.B.G.8
  • 45
    • 84925446149 scopus 로고    scopus 로고
    • Function through Synthesis-Informed Design
    • Wender, P. A.; Quiroz, R. V.; Stevens, M. C. Function through Synthesis-Informed Design Acc. Chem. Res. 2015, 48, 752-760 10.1021/acs.accounts.5b00004
    • (2015) Acc. Chem. Res. , vol.48 , pp. 752-760
    • Wender, P.A.1    Quiroz, R.V.2    Stevens, M.C.3
  • 46
    • 84925393362 scopus 로고    scopus 로고
    • The Chemical Space Project
    • Reymond, J. L. The Chemical Space Project Acc. Chem. Res. 2015, 48, 722-730 10.1021/ar500432k
    • (2015) Acc. Chem. Res. , vol.48 , pp. 722-730
    • Reymond, J.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.