The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides

Mohammad Aref Khalily, Hakan Usta (Corresponding Author), Mehmet Ozdemir, Gokhan Bakan, F. Begum Dikecoglu, Charlotte Edwards-Gayle, Jessica A. Hutchinson, Ian W. Hamley, Aykutlu Dana, Mustafa O. Guler (Corresponding Author)

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Abstract

π-Conjugated small molecules based on a [1]benzothieno[3,2-b]benzothiophene (BTBT) unit are of great research interest in the development of solution-processable semiconducting materials owing to their excellent charge-transport characteristics. However, the BTBT π-core has yet to be demonstrated in the form of electro-active one-dimensional (1D) nanowires that are self-assembled in aqueous media for potential use in bioelectronics and tissue engineering. Here we report the design, synthesis, and self-assembly of benzothienobenzothiophene (BTBT)-peptide conjugates, the BTBT-peptide (BTBT-C 3 -COHN-Ahx-VVAGKK-Am) and the C 8 -BTBT-peptide (C 8 -BTBT-C 3 -COHN-Ahx-VVAGKK-Am), as β-sheet forming amphiphilic molecules, which self-assemble into highly uniform nanofibers in water with diameters of 11-13(±1) nm and micron-size lengths. Spectroscopic characterization studies demonstrate the J-type π-π interactions among the BTBT molecules within the hydrophobic core of the self-assembled nanofibers yielding an electrical conductivity as high as 6.0 × 10 -6 S cm -1 . The BTBT π-core is demonstrated, for the first time, in the formation of self-assembled peptide 1D nanostructures in aqueous media for potential use in tissue engineering, bioelectronics and (opto)electronics. The conductivity achieved here is one of the highest reported to date in a non-doped state.

Original languageEnglish
Pages (from-to)9987-9995
Number of pages9
JournalNanoscale
Volume10
Issue number21
DOIs
Publication statusPublished - 7 Jun 2018

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Peptides
Nanowires
Bioelectric potentials
Semiconductor materials
Nanofibers
Tissue engineering
Fabrication
Molecules
Self assembly
Charge transfer
Nanostructures
Electronic equipment
Water
polypeptide C
Electric Conductivity
benzothiophene

Cite this

Khalily, M. A., Usta, H., Ozdemir, M., Bakan, G., Dikecoglu, F. B., Edwards-Gayle, C., ... Guler, M. O. (2018). The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides. Nanoscale, 10(21), 9987-9995. https://doi.org/10.1039/c8nr01604f
Khalily, Mohammad Aref ; Usta, Hakan ; Ozdemir, Mehmet ; Bakan, Gokhan ; Dikecoglu, F. Begum ; Edwards-Gayle, Charlotte ; Hutchinson, Jessica A. ; Hamley, Ian W. ; Dana, Aykutlu ; Guler, Mustafa O. / The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides. In: Nanoscale. 2018 ; Vol. 10, No. 21. pp. 9987-9995.
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title = "The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides",
abstract = "π-Conjugated small molecules based on a [1]benzothieno[3,2-b]benzothiophene (BTBT) unit are of great research interest in the development of solution-processable semiconducting materials owing to their excellent charge-transport characteristics. However, the BTBT π-core has yet to be demonstrated in the form of electro-active one-dimensional (1D) nanowires that are self-assembled in aqueous media for potential use in bioelectronics and tissue engineering. Here we report the design, synthesis, and self-assembly of benzothienobenzothiophene (BTBT)-peptide conjugates, the BTBT-peptide (BTBT-C 3 -COHN-Ahx-VVAGKK-Am) and the C 8 -BTBT-peptide (C 8 -BTBT-C 3 -COHN-Ahx-VVAGKK-Am), as β-sheet forming amphiphilic molecules, which self-assemble into highly uniform nanofibers in water with diameters of 11-13(±1) nm and micron-size lengths. Spectroscopic characterization studies demonstrate the J-type π-π interactions among the BTBT molecules within the hydrophobic core of the self-assembled nanofibers yielding an electrical conductivity as high as 6.0 × 10 -6 S cm -1 . The BTBT π-core is demonstrated, for the first time, in the formation of self-assembled peptide 1D nanostructures in aqueous media for potential use in tissue engineering, bioelectronics and (opto)electronics. The conductivity achieved here is one of the highest reported to date in a non-doped state.",
author = "Khalily, {Mohammad Aref} and Hakan Usta and Mehmet Ozdemir and Gokhan Bakan and Dikecoglu, {F. Begum} and Charlotte Edwards-Gayle and Hutchinson, {Jessica A.} and Hamley, {Ian W.} and Aykutlu Dana and Guler, {Mustafa O.}",
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Khalily, MA, Usta, H, Ozdemir, M, Bakan, G, Dikecoglu, FB, Edwards-Gayle, C, Hutchinson, JA, Hamley, IW, Dana, A & Guler, MO 2018, 'The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides' Nanoscale, vol. 10, no. 21, pp. 9987-9995. https://doi.org/10.1039/c8nr01604f

The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides. / Khalily, Mohammad Aref; Usta, Hakan (Corresponding Author); Ozdemir, Mehmet; Bakan, Gokhan; Dikecoglu, F. Begum; Edwards-Gayle, Charlotte; Hutchinson, Jessica A.; Hamley, Ian W.; Dana, Aykutlu; Guler, Mustafa O. (Corresponding Author).

In: Nanoscale, Vol. 10, No. 21, 07.06.2018, p. 9987-9995.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - The design and fabrication of supramolecular semiconductor nanowires formed by benzothienobenzothiophene (BTBT)-conjugated peptides

AU - Khalily, Mohammad Aref

AU - Usta, Hakan

AU - Ozdemir, Mehmet

AU - Bakan, Gokhan

AU - Dikecoglu, F. Begum

AU - Edwards-Gayle, Charlotte

AU - Hutchinson, Jessica A.

AU - Hamley, Ian W.

AU - Dana, Aykutlu

AU - Guler, Mustafa O.

PY - 2018/6/7

Y1 - 2018/6/7

N2 - π-Conjugated small molecules based on a [1]benzothieno[3,2-b]benzothiophene (BTBT) unit are of great research interest in the development of solution-processable semiconducting materials owing to their excellent charge-transport characteristics. However, the BTBT π-core has yet to be demonstrated in the form of electro-active one-dimensional (1D) nanowires that are self-assembled in aqueous media for potential use in bioelectronics and tissue engineering. Here we report the design, synthesis, and self-assembly of benzothienobenzothiophene (BTBT)-peptide conjugates, the BTBT-peptide (BTBT-C 3 -COHN-Ahx-VVAGKK-Am) and the C 8 -BTBT-peptide (C 8 -BTBT-C 3 -COHN-Ahx-VVAGKK-Am), as β-sheet forming amphiphilic molecules, which self-assemble into highly uniform nanofibers in water with diameters of 11-13(±1) nm and micron-size lengths. Spectroscopic characterization studies demonstrate the J-type π-π interactions among the BTBT molecules within the hydrophobic core of the self-assembled nanofibers yielding an electrical conductivity as high as 6.0 × 10 -6 S cm -1 . The BTBT π-core is demonstrated, for the first time, in the formation of self-assembled peptide 1D nanostructures in aqueous media for potential use in tissue engineering, bioelectronics and (opto)electronics. The conductivity achieved here is one of the highest reported to date in a non-doped state.

AB - π-Conjugated small molecules based on a [1]benzothieno[3,2-b]benzothiophene (BTBT) unit are of great research interest in the development of solution-processable semiconducting materials owing to their excellent charge-transport characteristics. However, the BTBT π-core has yet to be demonstrated in the form of electro-active one-dimensional (1D) nanowires that are self-assembled in aqueous media for potential use in bioelectronics and tissue engineering. Here we report the design, synthesis, and self-assembly of benzothienobenzothiophene (BTBT)-peptide conjugates, the BTBT-peptide (BTBT-C 3 -COHN-Ahx-VVAGKK-Am) and the C 8 -BTBT-peptide (C 8 -BTBT-C 3 -COHN-Ahx-VVAGKK-Am), as β-sheet forming amphiphilic molecules, which self-assemble into highly uniform nanofibers in water with diameters of 11-13(±1) nm and micron-size lengths. Spectroscopic characterization studies demonstrate the J-type π-π interactions among the BTBT molecules within the hydrophobic core of the self-assembled nanofibers yielding an electrical conductivity as high as 6.0 × 10 -6 S cm -1 . The BTBT π-core is demonstrated, for the first time, in the formation of self-assembled peptide 1D nanostructures in aqueous media for potential use in tissue engineering, bioelectronics and (opto)electronics. The conductivity achieved here is one of the highest reported to date in a non-doped state.

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