Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules

Unsal Koldemir; Jonathan S. Tinkham; Robert Johnson; Bogyu Lim; Henok A. Yemam; Kevin J. Gagnon; Sean Parkin; Alan Sellinger

doi:10.1039/c7tc02528a

Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules

Unsal Koldemir
, Jonathan S. Tinkham
, Robert Johnson
, Bogyu Lim
, Henok A. Yemam
, Kevin J. Gagnon
, Sean Parkin
, Alan Sellinger

Chemistry

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.

Original language	English
Pages (from-to)	8723-8733
Number of pages	11
Journal	Journal of Materials Chemistry C
Volume	5
Issue number	34
DOIs	https://doi.org/10.1039/c7tc02528a
State	Published - 2017

Bibliographical note

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

Funding

This work was partially supported by funds provided by the Global Climate and Energy Project (GCEP) award # 1138721 and by the Center for Advanced Molecular Photovoltaics (CAMP), award # KUS-C1-015-21 made by the King Abdullah University of Science and Technology (KAUST). Funding was also provided by the Research Corporation for Science Advancement (RCSA) through the Scialog Collaborative Innovation Award (#22355), and start up funds from the Colorado School of Mines (AS). We thank Prof. Alberto Salleo and Ms Camila Arantxa Cendra Guinassi from Stanford University, Department of Materials Science and Engineering for their help in testing these materials in organic field-effect transistors (OFETs). The Advanced Light Source is supported by the Director, Office of Science, Office of Basic Energy Sciences of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231. Crystallographic data for the structures reported in this paper have been deposited with the CCDC 1526927 and 1526928.†

Funders	Funder number
Center for Advanced Molecular Photovoltaics	KUS-C1-015-21
Office of Basic Energy Sciences
U.S. Department of Energy EPSCoR
Research Corporation for Science Advancement	22355
Research Corporation for Science Advancement
Office of Science Programs
Colorado School of Mines
King Abdullah University of Science and Technology

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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10.1039/c7tc02528a

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title = "Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules",

abstract = "A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange \#3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.",

author = "Unsal Koldemir and Tinkham, \{Jonathan S.\} and Robert Johnson and Bogyu Lim and Yemam, \{Henok A.\} and Gagnon, \{Kevin J.\} and Sean Parkin and Alan Sellinger",

note = "Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7tc02528a",

language = "English",

volume = "5",

pages = "8723--8733",

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AU - Koldemir, Unsal

AU - Tinkham, Jonathan S.

AU - Johnson, Robert

AU - Lim, Bogyu

AU - Yemam, Henok A.

AU - Gagnon, Kevin J.

AU - Parkin, Sean

AU - Sellinger, Alan

PY - 2017

Y1 - 2017

N2 - A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.

AB - A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.

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ER -

Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules

Abstract

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