skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors

Abstract

Combining core annulation and peripheral group modification, we have demonstrated a divergent synthesis of a family of highly functionalized coronene derivatives from a readily accessible dichlorodiazaperylene intermediate. Various reactions, such as aromatic nucleophilic substitution, Kumada coupling and Suzuki coupling proceed effectively on α-positions of the pyridine sites, giving rise to alkoxy, thioalkyl, alkyl or aryl substituted polycyclic aromatic hydrocarbons. In addition to peripheral group modulation, the aromatic core structures can be altered by annulation with thiophene or benzene ring systems. Corresponding single crystal X-ray diffraction and optical studies indicate that the heteroatom linkages not only impact the solid state packing, but also significantly influence the optoelectronic properties. Furthermore, these azacoronene derivatives display significant acid-induced spectroscopic changes, suggesting their great potential as colorimetric and fluorescence proton sensors.

Authors:
 [1];  [2];  [1];  [1];  [1];  [1];  [3];  [1];  [1]
  1. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  2. Zhejiang Univ., Hangzhou (China)
  3. Nanying Technological Univ. (Singapore)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Advanced Research Projects Agency - Energy (ARPA-E); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1214427
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 6; Journal Issue: 5; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

He, Bo, Dai, Jing, Zherebetskyy, Danylo, Chen, Teresa L., Zhang, Benjamin A., Teat, Simon J., Zhang, Qichun, Wang, Linwang, and Liu, Yi. A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors. United States: N. p., 2015. Web. doi:10.1039/C5SC00304K.
He, Bo, Dai, Jing, Zherebetskyy, Danylo, Chen, Teresa L., Zhang, Benjamin A., Teat, Simon J., Zhang, Qichun, Wang, Linwang, & Liu, Yi. A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors. United States. doi:10.1039/C5SC00304K.
He, Bo, Dai, Jing, Zherebetskyy, Danylo, Chen, Teresa L., Zhang, Benjamin A., Teat, Simon J., Zhang, Qichun, Wang, Linwang, and Liu, Yi. Tue . "A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors". United States. doi:10.1039/C5SC00304K. https://www.osti.gov/servlets/purl/1214427.
@article{osti_1214427,
title = {A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors},
author = {He, Bo and Dai, Jing and Zherebetskyy, Danylo and Chen, Teresa L. and Zhang, Benjamin A. and Teat, Simon J. and Zhang, Qichun and Wang, Linwang and Liu, Yi},
abstractNote = {Combining core annulation and peripheral group modification, we have demonstrated a divergent synthesis of a family of highly functionalized coronene derivatives from a readily accessible dichlorodiazaperylene intermediate. Various reactions, such as aromatic nucleophilic substitution, Kumada coupling and Suzuki coupling proceed effectively on α-positions of the pyridine sites, giving rise to alkoxy, thioalkyl, alkyl or aryl substituted polycyclic aromatic hydrocarbons. In addition to peripheral group modulation, the aromatic core structures can be altered by annulation with thiophene or benzene ring systems. Corresponding single crystal X-ray diffraction and optical studies indicate that the heteroatom linkages not only impact the solid state packing, but also significantly influence the optoelectronic properties. Furthermore, these azacoronene derivatives display significant acid-induced spectroscopic changes, suggesting their great potential as colorimetric and fluorescence proton sensors.},
doi = {10.1039/C5SC00304K},
journal = {Chemical Science},
number = 5,
volume = 6,
place = {United States},
year = {Tue Mar 31 00:00:00 EDT 2015},
month = {Tue Mar 31 00:00:00 EDT 2015}
}

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

Citation Metrics:
Cited by: 24 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Solution Processable Fluorenyl Hexa-peri-hexabenzocoronenes in Organic Field-Effect Transistors and Solar Cells
journal, March 2010

  • Wong, Wallace W. H.; Singh, T. Birendra; Vak, Doojin
  • Advanced Functional Materials, Vol. 20, Issue 6, p. 927-938
  • DOI: 10.1002/adfm.200901827

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions
journal, May 2009

  • Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G.
  • The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396
  • DOI: 10.1021/jp810292n