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

Title: Extended Ladder‐Type Benzo[ k ]tetraphene‐Derived Oligomers

Journal Article · · Angewandte Chemie
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [3];  [1]; ORCiD logo [2]; ORCiD logo [4]
  1. Department of Chemistry Texas A&,M University 3255 TAMU College Station TX 77843-3255 USA
  2. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering Zhejiang University 38 Zheda Rd Hangzhou 310027 China
  3. Department of Materials Science and Engineering Texas A&,M University 3003 TAMU College Station TX 77843-3003 USA
  4. Department of Chemistry Texas A&,M University 3255 TAMU College Station TX 77843-3255 USA, Department of Materials Science and Engineering Texas A&,M University 3003 TAMU College Station TX 77843-3003 USA

Abstract Well‐defined, fused‐ring aromatic oligomers represent promising candidates for the fundamental understanding and application of advanced carbon‐rich materials, though bottom‐up synthesis and structure–property correlation of these compounds remain challenging. In this work, an efficient synthetic route was employed to construct extended benzo[ k ]tetraphene‐derived oligomers with up to 13 fused rings. The molecular and electronic structures of these compounds were clearly elucidated. Precise correlation of molecular sizes and crystallization dynamics was established, thus demonstrating the pivotal balance between intermolecular interaction and molecular mobility for optimized processing of highly ordered solids of these extended conjugated molecules.

Sponsoring Organization:
USDOE
OSTI ID:
1395908
Journal Information:
Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 129 Journal Issue: 44; ISSN 0044-8249
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (37)

Regiocontrolled Synthesis of Ethene-Bridged para -Phenylene Oligomers Based on Pt II - and Ru II -Catalyzed Aromatization journal February 2010
Synthesis of Dibenz[ a , h ]anthracenes by Pd-Catalyzed Intramolecular Double-cyclization of ( Z , Z )- p -Styrylstilbenes journal March 2012
Fused Polycyclic Aromatics via Electrophile-Induced Cyclization Reactions: Application to the Synthesis of Graphite Ribbons journal August 1994
Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties journal July 2016
Nonlinear Optical Materials for the Smart Filtering of Optical Radiation journal October 2016
High-mobility polymer gate dielectric pentacene thin film transistors journal November 2002
Synthesis of Ladder-Type Thienoacenes and Their Electronic and Optical Properties journal January 2016
Phenacenes:  A Family of Graphite Ribbons. 2. Syntheses of Some [7]Phenacenes and an [11]Phenacene by Stilbene-like Photocyclizations journal March 1997
Non-linear, cata -Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties journal June 2015
Highly Efficient Multiphoton-Pumped Frequency-Upconversion Stimulated Blue Emission with Ultralow Threshold from Highly Extended Ladder-Type Oligo( p -phenylene)s journal August 2016
The Annellation Principle book January 1964
Research in Macromolecular Science: Challenges and Opportunities for the Next Decade journal January 2009
Höhere Acene: vielseitige organische Halbleiter journal January 2008
Ladder‐type Heteroarenes: Up to 15 Rings with Five Imide Groups journal June 2017
Die chemische Synthese von Nanographen, Graphen-Nanobändern und Graphen-Schichten journal July 2012
Forever young: polycyclic aromatic hydrocarbons as model cases for structural and optical studies journal January 2010
Molecular Coplanarity and Self-Assembly Promoted by Intramolecular Hydrogen Bonds journal November 2016
Intramolecular Charge Transport along Isolated Chains of Conjugated Polymers:  Effect of Torsional Disorder and Polymerization Defects journal August 2002
Fused Thiophene-Pyrrole-Containing Ring Systems up to a Heterodecacene journal July 2015
Highly Efficient Multiphoton-Pumped Frequency-Upconversion Stimulated Blue Emission with Ultralow Threshold from Highly Extended Ladder-Type Oligo( p -phenylene)s journal August 2016
The Larger Acenes: Versatile Organic Semiconductors journal January 2008
Phenyl Groups versus tert -Butyl Groups as Solubilizing Substituents for Some [5]Phenacenes and [7]Phenacenes journal August 2012
Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties journal July 2016
Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization journal July 2017
Convenient Synthesis of Dibenzo[ a , h ]anthracenes and Picenes via C–H Arylation of Acetophenones with Arenediboronates journal March 2011
Polycyclic Aromatic Hydrocarbons by Ring-Closing Metathesis journal October 2005
Ladder-type Heteroarenes: Up to 15 Rings with Five Imide Groups journal June 2017
Thermodynamic synthesis of solution processable ladder polymers journal January 2016
Synthesis of a carbon nanobelt journal April 2017
Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization journal July 2017
Low voltage operation in picene thin film field-effect transistor and its physical characteristics journal November 2009
On the conjugation length in poly( para -phenylene)-type polymers journal March 1995
Air-assisted High-performance Field-effect Transistor with Thin Films of Picene journal August 2008
Ambipolar charge transport of TIPS-pentacene single-crystals grown from non-polar solvents journal January 2015
Thermodynamics of the Segregation of a Kinetically Trapped Two-Dimensional Amorphous Metal–Organic Network journal February 2016
From Nanographene and Graphene Nanoribbons to Graphene Sheets: Chemical Synthesis journal July 2012
Anellierte Thiophen-Pyrrol-haltige Ringsysteme bis zu einem Heterodecacen journal July 2015

Similar Records

Extended Ladder-Type Benzo[k]tetraphene-Derived Oligomers
Journal Article · Fri Sep 08 00:00:00 EDT 2017 · Angewandte Chemie (International Edition) · OSTI ID:1395908

Ladder Oligo(m-aniline)s: Derivatives of Azaacenes with Cross-Conjugated [pi]-Systems
Journal Article · Mon Apr 30 00:00:00 EDT 2012 · Journal of Organic Chemistry · OSTI ID:1395908

Naphthodithiophene‐Based Nonfullerene Acceptor for High‐Performance Organic Photovoltaics: Effect of Extended Conjugation
Journal Article · Thu Nov 23 00:00:00 EST 2017 · Advanced Materials · OSTI ID:1395908

Related Subjects