DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: 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:
 [1];  [1];  [1];  [1];  [1];  [2];  [1];  [1]
  1. Department of Chemistry New York University New York NY 10003 USA
  2. Department of Chemistry Purdue University West Lafayette IN 47907 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1399624
Grant/Contract Number:  
SC0007991
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie
Additional Journal Information:
Journal Name: Angewandte Chemie Journal Volume: 129 Journal Issue: 23; Journal ID: ISSN 0044-8249
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

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. Germany: N. p., 2017. Web. doi:10.1002/ange.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. Germany. https://doi.org/10.1002/ange.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". Germany. https://doi.org/10.1002/ange.201700462.
@article{osti_1399624,
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/ange.201700462},
journal = {Angewandte Chemie},
number = 23,
volume = 129,
place = {Germany},
year = {Wed May 03 00:00:00 EDT 2017},
month = {Wed May 03 00:00:00 EDT 2017}
}

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
  • DOI: 10.1021/ma0021287

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
  • DOI: 10.1002/jrs.2007

“Synthetic Metals”: A Novel Role for Organic Polymers (Nobel Lecture)
journal, July 2001


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
  • DOI: 10.1021/ja0648413

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
  • DOI: 10.1021/ja00286a057

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
  • DOI: 10.1002/ange.201309914

Controlled Trapping and Release of Quantum Dots in a DNA-Switchable Hydrogel
journal, October 2007


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
  • DOI: 10.1039/C5SC02203G

“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
  • DOI: 10.1080/00268948508074857

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
  • DOI: 10.1021/jacs.6b10458

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
  • DOI: 10.1021/cm501445u

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
  • DOI: 10.1021/ja1014184

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
  • DOI: 10.1093/protein/1.4.295

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
  • DOI: 10.1021/ja00064a070

Molecular rectifiers
journal, November 1974


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
  • DOI: 10.1021/nn305424e

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
  • DOI: 10.1002/jrs.1841

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
  • DOI: 10.1063/1.115797

Raman and infrared spectra of polyaniline
journal, February 1987


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
  • DOI: 10.1021/ja104833t

Raman Spectrum of Graphene and Graphene Layers
journal, October 2006


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
  • DOI: 10.1038/nature08274

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
  • DOI: 10.1021/ja980052c

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
  • DOI: 10.1038/nnano.2015.190

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
  • DOI: 10.1002/anie.201309914

‘Polyaniline’: Protonic acid doping of the emeraldine form to the metallic regime
journal, January 1986