Modular electron donor group tuning of frontier energy levels in diarylaminofluorenone push–pull molecules

Homnick, Paul J.; Lahti, Paul M.

doi:10.1039/c2cp41813d

Title: Modular electron donor group tuning of frontier energy levels in diarylaminofluorenone push–pull molecules

Journal Article · Sun Jan 01 00:00:00 EST 2012 · Physical Chemistry Chemical Physics. PCCP (Print)

DOI:https://doi.org/10.1039/c2cp41813d· OSTI ID:1382353

Homnick, Paul J.; Lahti, Paul M.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Polymer-Based Materials for Harvesting Solar Energy (PHaSE)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001087

OSTI ID:: 1382353

Journal Information:: Physical Chemistry Chemical Physics. PCCP (Print), Vol. 14, Issue 34; Related Information: PHaSE partners with University of Massachusetts, Amherst (lead) and Lowell; Oak Ridge National Laboratory; Pennsylvania State University; Renssalaer Polytechnic Institute; University of Pittsburgh; ISSN 1463-9076

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (30)

Electric Field Poled Organic Electro-optic Materials: State of the Art and Future Prospects Dalton, Larry R.; Sullivan, Philip A.; Bale, Denise H. Chemical Reviews, Vol. 110, Issue 1 https://doi.org/10.1021/cr9000429	journal	January 2010
Density Functionals with Broad Applicability in Chemistry Zhao, Yan; Truhlar, Donald G. Accounts of Chemical Research, Vol. 41, Issue 2 https://doi.org/10.1021/ar700111a	journal	February 2008
New software for searching the Cambridge Structural Database and visualizing crystal structures Bruno, Ian J.; Cole, Jason C.; Edgington, Paul R. Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3 https://doi.org/10.1107/S0108768102003324	journal	May 2002
Polyfluorene with p-carborane in the backbone Peterson, Joseph J.; Simon, Yoan C.; Coughlin, E. Bryan Chemical Communications, Issue 33 https://doi.org/10.1039/b908131c	journal	January 2009
Nonlinear optical properties of quasilinear conjugated oligomers, polymers and organic molecules Kirtman, Bernard; Champagne, Benoit International Reviews in Physical Chemistry, Vol. 16, Issue 4 https://doi.org/10.1080/014423597230181	journal	October 1997
Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Zhou, Huaxing; Yang, Liqiang; You, Wei Macromolecules, Vol. 45, Issue 2 https://doi.org/10.1021/ma201648t	journal	January 2012
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
On the nature of the fluorenone-based emission in oxidized poly(dialkyl-fluorene)s Ferenczi, T. A. M.; Sims, M.; Bradley, D. D. C. Journal of Physics: Condensed Matter, Vol. 20, Issue 4 https://doi.org/10.1088/0953-8984/20/04/045220	journal	January 2008
Fluorenone‐Based Molecules for Bulk‐Heterojunction Solar Cells: Synthesis, Characterization, and Photovoltaic Properties Lincker, Frédéric; Delbosc, Nicolas; Bailly, Séverine Advanced Functional Materials, Vol. 18, Issue 21 https://doi.org/10.1002/adfm.200800366	journal	November 2008
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank Chemical Reviews, Vol. 88, Issue 6 https://doi.org/10.1021/cr00088a005	journal	September 1988
Bulky Alkylphosphines with Neopentyl Substituents as Ligands in the Amination of Aryl Bromides and Chlorides Hill, Lensey L.; Moore, Lucas R.; Huang, Rongcai The Journal of Organic Chemistry, Vol. 71, Issue 14 https://doi.org/10.1021/jo060303x	journal	June 2006
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Low band gap polymers for organic photovoltaics Bundgaard, Eva; Krebs, Frederik C. Solar Energy Materials and Solar Cells, Vol. 91, Issue 11, p. 954-985 https://doi.org/10.1016/j.solmat.2007.01.015	journal	July 2007
Synthesis and electroluminescence of novel copolymers containing crown ether spacers Sun, Qingjiang; Wang, Haiqiao; Yang, Chunhe Journal of Materials Chemistry, Vol. 13, Issue 4 https://doi.org/10.1039/b209469j	journal	February 2003
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Palladium-catalyzed amination of aryl halides and sulfonates Yang, Bryant H.; Buchwald, Stephen L. Journal of Organometallic Chemistry, Vol. 576, Issue 1-2 https://doi.org/10.1016/S0022-328X(98)01054-7	journal	March 1999
Signaling Recognition Events with Fluorescent Sensors and Switches de Silva, A. Prasanna; Gunaratne, H. Q. Nimal; Gunnlaugsson, Thorfinnur Chemical Reviews, Vol. 97, Issue 5 https://doi.org/10.1021/cr960386p	journal	August 1997
Efficient two layer leds on a polymer blend basis Pommerehne, Jörn; Vestweber, Horst; Guss, Werner Advanced Materials, Vol. 7, Issue 6 https://doi.org/10.1002/adma.19950070608	journal	June 1995
Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications Beaujuge, Pierre M.; Fréchet, Jean M. J. Journal of the American Chemical Society, Vol. 133, Issue 50, p. 20009-20029 https://doi.org/10.1021/ja2073643	journal	December 2011
Conjugated Oligomers with Terminal Donor–Acceptor Substitution Meier, Herbert Angewandte Chemie International Edition, Vol. 44, Issue 17 https://doi.org/10.1002/anie.200461146	journal	April 2005
Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications Cardona, Claudia M.; Li, Wei; Kaifer, Angel E. Advanced Materials, Vol. 23, Issue 20 https://doi.org/10.1002/adma.201004554	journal	April 2011
Structures and properties of conjugated Donor–Acceptor copolymers for solar cell applications Zhang, Zhi–Guo; Wang, Jizheng Journal of Materials Chemistry, Vol. 22, Issue 10 https://doi.org/10.1039/c2jm14951f	journal	January 2012
Processable Low-Bandgap Polymers for Photovoltaic Applications ^† Boudreault, Pierre-Luc T.; Najari, Ahmed; Leclerc, Mario Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm1021855	journal	February 2011
Recent progress in second-order nonlinear optical polymers and dendrimers Cho, Min Ju; Choi, Dong Hoon; Sullivan, Philip A. Progress in Polymer Science, Vol. 33, Issue 11 https://doi.org/10.1016/j.progpolymsci.2008.07.007	journal	November 2008
The Cambridge Structural Database: a quarter of a million crystal structures and rising Allen, Frank H. Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3 https://doi.org/10.1107/S0108768102003890	journal	May 2002
Electrochemical bandgaps of substituted polythiophenes Johansson, Tomas; Mammo, Wendimagegn; Svensson, Mattias J. Mater. Chem., Vol. 13, Issue 6 https://doi.org/10.1039/B301403G	journal	January 2003
Intermolecular Hydrogen Bonds Induce Highly Emissive Excimers: Enhancement of Solid-State Luminescence Liu, Yang; Tao, Xutang; Wang, Fuzhi The Journal of Physical Chemistry C, Vol. 111, Issue 17 https://doi.org/10.1021/jp070288f	journal	May 2007
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems Roncali, Jean Chemical Reviews, Vol. 97, Issue 1 https://doi.org/10.1021/cr950257t	journal	February 1997
Stabilized Blue Emission from Polyfluorene-Based Light-Emitting Diodes: Elimination of Fluorenone Defects Gong, X.; Iyer, P. K.; Moses, D. Advanced Functional Materials, Vol. 13, Issue 4 https://doi.org/10.1002/adfm.200304279	journal	April 2003

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Title: Modular electron donor group tuning of frontier energy levels in diarylaminofluorenone push–pull molecules

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