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

Title: A bundled-stack discotic columnar liquid crystalline phase with inter-stack electronic coupling

Abstract

The first compound proving to be capable of forming a bundled-stack discotic columnar liquid crystalline (BSDCLC) phase was designed and synthesized. Finally, the unique perylene anhydride inter-stack interaction was found to be the key to the formation of the BSDCLC structure and inter-stack electronic coupling (ISEC).

Authors:
 [1];  [1];  [2];  [1];  [2];  [3];  [1]
  1. City Univ. of New York, Staten Island, NY (United States). College of Staten Island. Dept. of Chemistry. Center for Engineered Polymeric Materials
  2. Delft Univ. of Technology (Netherlands). DelftChemTech
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences Division
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS); City Univ. of New York, Staten Island, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC); National Science Foundation (NSF); City Univ. of New York (United States); Netherlands Organization for Scientific Research (NWO); European Research Council (ERC)
Contributing Org.:
Delft Univ. of Technology (Netherlands)
OSTI Identifier:
1265545
Grant/Contract Number:  
AC05-00OR22725; CHE-0723028; FP7/2007-2013; 240299
Resource Type:
Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 51; Journal Issue: 59; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Wang, Bin, Sun, Runkun, Günbaş, Duygu D., Zhang, Hao, Grozema, Ferdinand C., Xiao, Kai, and Jin, Shi. A bundled-stack discotic columnar liquid crystalline phase with inter-stack electronic coupling. United States: N. p., 2015. Web. doi:10.1039/C5CC03789A.
Wang, Bin, Sun, Runkun, Günbaş, Duygu D., Zhang, Hao, Grozema, Ferdinand C., Xiao, Kai, & Jin, Shi. A bundled-stack discotic columnar liquid crystalline phase with inter-stack electronic coupling. United States. https://doi.org/10.1039/C5CC03789A
Wang, Bin, Sun, Runkun, Günbaş, Duygu D., Zhang, Hao, Grozema, Ferdinand C., Xiao, Kai, and Jin, Shi. Mon . "A bundled-stack discotic columnar liquid crystalline phase with inter-stack electronic coupling". United States. https://doi.org/10.1039/C5CC03789A. https://www.osti.gov/servlets/purl/1265545.
@article{osti_1265545,
title = {A bundled-stack discotic columnar liquid crystalline phase with inter-stack electronic coupling},
author = {Wang, Bin and Sun, Runkun and Günbaş, Duygu D. and Zhang, Hao and Grozema, Ferdinand C. and Xiao, Kai and Jin, Shi},
abstractNote = {The first compound proving to be capable of forming a bundled-stack discotic columnar liquid crystalline (BSDCLC) phase was designed and synthesized. Finally, the unique perylene anhydride inter-stack interaction was found to be the key to the formation of the BSDCLC structure and inter-stack electronic coupling (ISEC).},
doi = {10.1039/C5CC03789A},
journal = {ChemComm},
number = 59,
volume = 51,
place = {United States},
year = {Mon Jun 15 00:00:00 EDT 2015},
month = {Mon Jun 15 00:00:00 EDT 2015}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 9 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Assembly and Fiber Formation of a Gemini-Type Hexathienocoronene Amphiphile for Electrical Conduction
journal, August 2013

  • Chen, Long; Mali, Kunal S.; Puniredd, Sreenivasa R.
  • Journal of the American Chemical Society, Vol. 135, Issue 36
  • DOI: 10.1021/ja4062135

High Electron Mobility in Room-Temperature Discotic Liquid-Crystalline Perylene Diimides
journal, November 2005


Functional Liquid-Crystalline Assemblies: Self-Organized Soft Materials
journal, January 2006

  • Kato, Takashi; Mizoshita, Norihiro; Kishimoto, Kenji
  • Angewandte Chemie International Edition, Vol. 45, Issue 1
  • DOI: 10.1002/anie.200501384

About Supramolecular Assemblies of π-Conjugated Systems
journal, April 2005

  • Hoeben, Freek J. M.; Jonkheijm, Pascal; Meijer, E. W.
  • Chemical Reviews, Vol. 105, Issue 4
  • DOI: 10.1021/cr030070z

Discotic liquid crystals: a new generation of organic semiconductors
journal, January 2007

  • Sergeyev, Sergey; Pisula, Wojciech; Geerts, Yves Henri
  • Chemical Society Reviews, Vol. 36, Issue 12
  • DOI: 10.1039/b417320c

Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics
journal, August 2001


Face-on Oriented Bilayer of Two Discotic Columnar Liquid Crystals for Organic Donor−Acceptor Heterojunction
journal, May 2010

  • Thiebaut, Olivier; Bock, Harald; Grelet, Eric
  • Journal of the American Chemical Society, Vol. 132, Issue 20
  • DOI: 10.1021/ja1012596

Partially stripped insulated nanowires: a lightly substituted hexa-peri-hexabenzocoronene-based columnar liquid crystal
journal, January 2004

  • Wang, Zhaohui; Watson, Mark D.; Wu, Jishan
  • Chem. Commun., Issue 3
  • DOI: 10.1039/B311651D

Tuning the Columnar Organization of Discotic Polycyclic Aromatic Hydrocarbons
journal, August 2010

  • Pisula, Wojciech; Feng, Xinliang; Müllen, Klaus
  • Advanced Materials, Vol. 22, Issue 33
  • DOI: 10.1002/adma.201000585

Columnar Mesophases Based on Zinc Chlorophyll Derivatives Functionalized with Peripheral Dendron Wedges
journal, April 2011

  • Sengupta, Sanchita; Uemura, Shinobu; Patwardhan, Sameer
  • Chemistry – A European Journal, Vol. 17, Issue 19
  • DOI: 10.1002/chem.201002659

Self-organization of supramolecular helical dendrimers into complex electronic materials
journal, September 2002


Self-Assembly of Semifluorinated Dendrons Attached to Electron-Donor Groups Mediates Their π-Stacking via a Helical Pyramidal Column
journal, August 2006

  • Percec, Virgil; Glodde, Martin; Peterca, Mihai
  • Chemistry - A European Journal, Vol. 12, Issue 24
  • DOI: 10.1002/chem.200501195

Self-Assembly of Semifluorinated Minidendrons Attached to Electron-Acceptor Groups into Pyramidal Columns
journal, April 2007

  • Percec, Virgil; Aqad, Emad; Peterca, Mihai
  • Chemistry - A European Journal, Vol. 13, Issue 12
  • DOI: 10.1002/chem.200600901

The Core-Size Effect on the Mobility of Charge in Discotic Liquid Crystalline Materials
journal, January 2001


Liquid Crystalline Perylene Diimides:  Architecture and Charge Carrier Mobilities
journal, November 2000

  • Struijk, Corien W.; Sieval, Alexander B.; Dakhorst, Jarno E. J.
  • Journal of the American Chemical Society, Vol. 122, Issue 45
  • DOI: 10.1021/ja000991g

Non-conventional liquid crystals—the importance of micro-segregation for self-organisation
journal, January 1998

  • Tschierske, Carsten
  • Journal of Materials Chemistry, Vol. 8, Issue 7
  • DOI: 10.1039/a800946e

Self-Organized Perylene Diimide Nanofibers
journal, January 2005

  • Yan, Ping; Chowdhury, Arindam; Holman, Michael W.
  • The Journal of Physical Chemistry B, Vol. 109, Issue 2
  • DOI: 10.1021/jp046133e

A Room-Temperature Liquid-Crystalline Phase with Crystalline π Stacks
journal, May 2007

  • Xu, Yijin; Leng, Siwei; Xue, Chenming
  • Angewandte Chemie International Edition, Vol. 46, Issue 21
  • DOI: 10.1002/anie.200604607

Study of orientational ordering in discotic liquid-crystalline thin films by using Fourier transform infra-red spectroscopy
journal, September 1997


Monitoring surface molecular order in discotic liquid crystals
journal, March 2001


Structure and Phase Behavior of a Discotic Columnar Liquid Crystal Confined in Nanochannels
journal, August 2012

  • Cerclier, Carole V.; Ndao, Makha; Busselez, Rémi
  • The Journal of Physical Chemistry C, Vol. 116, Issue 35
  • DOI: 10.1021/jp303690q

Morphology of open films of discotic hexagonal columnar liquid crystals as probed by grazing incidence X-ray diffraction
journal, April 2010

  • Grelet, Eric; Dardel, Sébastien; Bock, Harald
  • The European Physical Journal E, Vol. 31, Issue 4
  • DOI: 10.1140/epje/i2010-10586-2

Dipole-dipole interactions in simple esters and in liquid-crystal polyesters
journal, May 1993


Photoluminescence and Conductivity of Self-Assembled π–π Stacks of Perylene Bisimide Dyes
journal, January 2007

  • Chen, Zhijian; Stepanenko, Vladimir; Dehm, Volker
  • Chemistry - A European Journal, Vol. 13, Issue 2
  • DOI: 10.1002/chem.200600889

Helical Growth of Semiconducting Columnar Dye Assemblies Based on Chiral Perylene Bisimides
journal, March 2007

  • Dehm, Volker; Chen, Zhijian; Baumeister, Ute
  • Organic Letters, Vol. 9, Issue 6
  • DOI: 10.1021/ol0700963

Relationship between supramolecular assembly and charge-carrier mobility in perylenediimide derivatives: The impact of side chains
journal, January 2011

  • May, Falk; Marcon, Valentina; Hansen, Michael Ryan
  • Journal of Materials Chemistry, Vol. 21, Issue 26
  • DOI: 10.1039/c1jm10500k

High electron mobility in a columnar phase of liquid-crystalline perylene tetracarboxylic bisimide bearing oligosiloxane chains
journal, January 2012

  • Funahashi, Masahiro; Sonoda, Akinari
  • Journal of Materials Chemistry, Vol. 22, Issue 48
  • DOI: 10.1039/c2jm35579e

Electron transport characteristics in nanosegregated columnar phases of perylene tetracarboxylic bisimide derivatives bearing oligosiloxane chains
journal, January 2014

  • Funahashi, Masahiro; Sonoda, Akinari
  • Phys. Chem. Chem. Phys., Vol. 16, Issue 17
  • DOI: 10.1039/C4CP00579A

Works referencing / citing this record: