An Organic Semiconductor Organized into 3D DNA Arrays by “Bottom-up” Rational Design
Abstract
Abstract A 3D array of organic semiconductors was assembled using a DNA scaffold. An octameric aniline molecule (“octaniline”) was incorporated into a DNA building block based on a dimeric tensegrity triangle. The construct self‐assembled to form a 3D crystal. Reversible redox conversion between the pernigraniline and leucoemeraldine states of the octaniline is retained in the crystal. Protonic doping gave emeraldine salt at pH 5, corresponding to the conductive form of polyaniline. Redox cycling within the crystal was visualized by color changes and Raman microscopy. The ease of conversion between the octaniline states suggests that it is a viable electronic switch within a unique 3D structure.
- Authors:
-
- New York Univ. (NYU), NY (United States)
- Purdue Univ., West Lafayette, IN (United States)
- Publication Date:
- Research Org.:
- New York Univ. (NYU), NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR); US Army Research Office (ARO); US Department of the Navy, Office of Naval Research (ONR); Gordon and Betty Moore Foundation
- OSTI Identifier:
- 1533098
- Alternate Identifier(s):
- OSTI ID: 1399620
- Grant/Contract Number:
- SC0007991; CHE-1412568; ODISSEI-1332411; CCF- 526650; W911NF-11-1-0024; N000141110729; GBMF3849
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 23; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry; Polyaniline; Self-assembly; Nanoelectronics; DNA tensegrity triangle; Crystal engineering
Citation Formats
Wang, Xiao, Sha, Ruojie, Kristiansen, Martin, Hernandez, Carina, Hao, Yudong, Mao, Chengde, Canary, James W., and Seeman, Nadrian C. An Organic Semiconductor Organized into 3D DNA Arrays by “Bottom-up” Rational Design. United States: N. p., 2017.
Web. doi:10.1002/anie.201700462.
Wang, Xiao, Sha, Ruojie, Kristiansen, Martin, Hernandez, Carina, Hao, Yudong, Mao, Chengde, Canary, James W., & Seeman, Nadrian C. An Organic Semiconductor Organized into 3D DNA Arrays by “Bottom-up” Rational Design. United States. https://doi.org/10.1002/anie.201700462
Wang, Xiao, Sha, Ruojie, Kristiansen, Martin, Hernandez, Carina, Hao, Yudong, Mao, Chengde, Canary, James W., and Seeman, Nadrian C. Wed .
"An Organic Semiconductor Organized into 3D DNA Arrays by “Bottom-up” Rational Design". United States. https://doi.org/10.1002/anie.201700462. https://www.osti.gov/servlets/purl/1533098.
@article{osti_1533098,
title = {An Organic Semiconductor Organized into 3D DNA Arrays by “Bottom-up” Rational Design},
author = {Wang, Xiao and Sha, Ruojie and Kristiansen, Martin and Hernandez, Carina and Hao, Yudong and Mao, Chengde and Canary, James W. and Seeman, Nadrian C.},
abstractNote = {Abstract A 3D array of organic semiconductors was assembled using a DNA scaffold. An octameric aniline molecule (“octaniline”) was incorporated into a DNA building block based on a dimeric tensegrity triangle. The construct self‐assembled to form a 3D crystal. Reversible redox conversion between the pernigraniline and leucoemeraldine states of the octaniline is retained in the crystal. Protonic doping gave emeraldine salt at pH 5, corresponding to the conductive form of polyaniline. Redox cycling within the crystal was visualized by color changes and Raman microscopy. The ease of conversion between the octaniline states suggests that it is a viable electronic switch within a unique 3D structure.},
doi = {10.1002/anie.201700462},
journal = {Angewandte Chemie (International Edition)},
number = 23,
volume = 56,
place = {United States},
year = {Wed May 03 00:00:00 EDT 2017},
month = {Wed May 03 00:00:00 EDT 2017}
}
Web of Science
Works referenced in this record:
Manipulating DNA Conformation Using Intertwined Conducting Polymer Chains †
journal, June 2001
- Nagarajan, Ramaswamy; Liu, Wei; Kumar, Jayant
- Macromolecules, Vol. 34, Issue 12
The chemical oxidative polymerization of aniline in water: Raman spectroscopy
journal, October 2008
- Ćirić-Marjanović, Gordana; Trchová, Miroslava; Stejskal, Jaroslav
- Journal of Raman Spectroscopy, Vol. 39, Issue 10
“Synthetic Metals”: A Novel Role for Organic Polymers (Nobel Lecture)
journal, July 2001
- MacDiarmid, Alan G.
- Angewandte Chemie International Edition, Vol. 40, Issue 14
DNA-Directed Assembly of Polyanilines: Modified Cytosine Nucleotides Transfer Sequence Programmability to a Conjoined Polymer
journal, November 2006
- Datta, Bhaskar; Schuster, Gary B.; McCook, Amanda
- Journal of the American Chemical Society, Vol. 128, Issue 45
Phenyl-capped octaaniline (COA): an excellent model for polyaniline
journal, December 1986
- Lu, F. L.; Wudl, Fred.; Nowak, M.
- Journal of the American Chemical Society, Vol. 108, Issue 26
Functionalizing Designer DNA Crystals with a Triple-Helical Veneer
journal, March 2014
- Rusling, David A.; Chandrasekaran, Arun Richard; Ohayon, Yoel P.
- Angewandte Chemie, Vol. 126, Issue 15
Controlled Trapping and Release of Quantum Dots in a DNA-Switchable Hydrogel
journal, October 2007
- Liedl, Tim; Dietz, Hendrik; Yurke, Bernard
- Small, Vol. 3, Issue 10
Hemin–G-quadruplex-crosslinked poly-N-isopropylacrylamide hydrogel: a catalytic matrix for the deposition of conductive polyaniline
journal, January 2015
- Lu, Chun-Hua; Guo, Weiwei; Qi, Xiu-Juan
- Chemical Science, Vol. 6, Issue 11
“Polyaniline”: Interconversion of Metallic and Insulating Forms
journal, March 1985
- Macdiarmid, Alan G.; Chiang, Jin-Chih; Halpern, Marc
- Molecular Crystals and Liquid Crystals, Vol. 121, Issue 1-4
Reversible Modulation of DNA-Based Hydrogel Shapes by Internal Stress Interactions
journal, December 2016
- Hu, Yuwei; Kahn, Jason S.; Guo, Weiwei
- Journal of the American Chemical Society, Vol. 138, Issue 49
Shape-Controlled Nanofabrication of Conducting Polymer on Planar DNA Templates
journal, June 2014
- Wang, Zhen-Gang; Liu, Qing; Ding, Baoquan
- Chemistry of Materials, Vol. 26, Issue 11
Nanoscale Morphology, Dimensional Control, and Electrical Properties of Oligoanilines
journal, August 2010
- Wang, Yue; Tran, Henry D.; Liao, Lei
- Journal of the American Chemical Society, Vol. 132, Issue 30
The design of a biochip: a self-assembling molecular-scale memory device
journal, January 1987
- Robinson, Bruce H.; Seeman, Nadrian C.
- "Protein Engineering, Design and Selection", Vol. 1, Issue 4
Self-orienting head-to-tail poly(3-alkylthiophenes): new insights on structure-property relationships in conducting polymers
journal, June 1993
- McCullough, Richard D.; Tristram-Nagle, Stephanie; Williams, Shawn P.
- Journal of the American Chemical Society, Vol. 115, Issue 11
Molecular rectifiers
journal, November 1974
- Aviram, Arieh; Ratner, Mark A.
- Chemical Physics Letters, Vol. 29, Issue 2
Self-Assembled Catalytic DNA Nanostructures for Synthesis of Para-directed Polyaniline
journal, January 2013
- Wang, Zhen-Gang; Zhan, Pengfei; Ding, Baoquan
- ACS Nano, Vol. 7, Issue 2
Studies on the resonance Raman spectra of polyaniline obtained with near‐IR excitation
journal, July 2008
- do Nascimento, Gustavo M.; Temperini, M´rcia L. A.
- Journal of Raman Spectroscopy, Vol. 39, Issue 7
Exciton diffusion and dissociation in a poly(p‐phenylenevinylene)/C60 heterojunction photovoltaic cell
journal, May 1996
- Halls, J. J. M.; Pichler, K.; Friend, R. H.
- Applied Physics Letters, Vol. 68, Issue 22, p. 3120-3122
Raman and infrared spectra of polyaniline
journal, February 1987
- Ohira, Manabu; Sakai, Toshiyuki; Takeuchi, Masataka
- Synthetic Metals, Vol. 18, Issue 1-3
A DNA Crystal Designed to Contain Two Molecules per Asymmetric Unit
journal, November 2010
- Wang, Tong; Sha, Ruojie; Birktoft, Jens
- Journal of the American Chemical Society, Vol. 132, Issue 44
Raman Spectrum of Graphene and Graphene Layers
journal, October 2006
- Ferrari, A. C.; Meyer, J. C.; Scardaci, V.
- Physical Review Letters, Vol. 97, Issue 18, Article No. 187401
From molecular to macroscopic via the rational design of a self-assembled 3D DNA crystal
journal, September 2009
- Zheng, Jianping; Birktoft, Jens J.; Chen, Yi
- Nature, Vol. 461, Issue 7260
„Synthetische Metalle“: eine neue Rolle für organische Polymere (Nobel-Vortrag)
journal, July 2001
- MacDiarmid, Alan G.
- Angewandte Chemie, Vol. 113, Issue 14
Palladium-Catalyzed Synthesis of Monodisperse, Controlled-Length, and Functionalized Oligoanilines
journal, May 1998
- Sadighi, Joseph P.; Singer, Robert A.; Buchwald, Stephen L.
- Journal of the American Chemical Society, Vol. 120, Issue 20
Routing of individual polymers in designed patterns
journal, August 2015
- Knudsen, Jakob Bach; Liu, Lei; Bank Kodal, Anne Louise
- Nature Nanotechnology, Vol. 10, Issue 10
Functionalizing Designer DNA Crystals with a Triple-Helical Veneer
journal, March 2014
- Rusling, David A.; Chandrasekaran, Arun Richard; Ohayon, Yoel P.
- Angewandte Chemie International Edition, Vol. 53, Issue 15
‘Polyaniline’: Protonic acid doping of the emeraldine form to the metallic regime
journal, January 1986
- Chiang, Jin-Chih; MacDiarmid, Alan G.
- Synthetic Metals, Vol. 13, Issue 1-3
Works referencing / citing this record:
DNA nanotechnology
journal, November 2017
- Seeman, Nadrian C.; Sleiman, Hanadi F.
- Nature Reviews Materials, Vol. 3, Issue 1
Ordered three-dimensional nanomaterials using DNA-prescribed and valence-controlled material voxels
journal, January 2020
- Tian, Ye; Lhermitte, Julien R.; Bai, Lin
- Nature Materials, Vol. 19, Issue 7
Three-dimensional molecular and nanoparticle crystallization by DNA nanotechnology
journal, December 2017
- Seeman, Nadrian C.; Gang, Oleg
- MRS Bulletin, Vol. 42, Issue 12
Gold Nanoparticles in Conjunction with Nucleic Acids as a Modern Molecular System for Cellular Delivery
journal, January 2020
- Graczyk, Anna; Pawlowska, Roza; Jedrzejczyk, Dominika
- Molecules, Vol. 25, Issue 1