John Anthony

Research Interests:
Aromatic Chemistry
Organic Semiconductors
Materials for flexible electronics
organic synthesis
Education

B. A. Reed College, Portland OR, 1989
Ph. D. University of California, Los Angeles, 1994

Research

Aromatic molecules are a robust and versatile platform for the development of functional materials for electronic and optical applications. Using a tandem organic synthesis / device analysis approach, we seek to determine structure-property relationships that lead to materials with exceptional performance in organic thin-film transistors (for flexible flat-panel displays), organic solar cells (for low-cost generation of electricity), organic light-emitting diodes (for high-efficiency lighting) and other applications. Needless to say, students in my group learn a wide range of skills, from organic synthesis to materials characterization and device fabrication.

We are also exploring new functionalization strategies to further enhance the stability of these strongly-absorbing molecules, for use in low-cost solar cells.

 

Materials: In collaboration with the UK X-ray crystallography facility, we have developed an excellent model that allows us to predict the solid-state order of acenes functionalized by our method - the fine-tuning allows us to make subtle changes that improve film morphology, electrode contacts or photostability. Following this model, we have prepared materials with record-high performance in a number of areas.

Transistors: A field-effect transistor is a three-electrode device that turns current between two of the electrodes (labeled "source" and "drain") off or on by application of voltage across the third electrode (called the "gate"). For use in organic transistors, we have obtained the best results using molecules that exhibit two-dimensional pi-stacking in the sold state. We collaborate with many physics and engineering research groups to discover the device performance of the materials we prepare.  For example, collaboration with the Loo group has shown new methods to control the crystal size in anthradithiophene materials, while the Jurchescu group has used spray-coating to form large-area transistor arrays with mobility as high as 5 cm2/Vs.

Solar Energy: Acenes undergo a process called 'singlet fission', which can turn one photon into two photons of roughly half the energy.  We are working on thin film materials that will convert high-energy light from the sun into double the amount of photons of lower energy, to boost the number of photons interacting with silicon solar cells. If we can do this efficiently, it will dramatically boost the power output of modern solar panels..

We are also exploring the use of functionalized carbon-based materials in a wide array of applications, including bio-imaging, thermoelectric power generation, radiation detection, and quantum information science.

I am grateful to all of my collaborators (many of whom are not mentioned on this short web page) for their insight, assistance, and for being such fantastic people to work with. I also thank the support (both intellectual and financial) of our research programs by the Office of Naval Research, the National Science Foundation, and the Department of Energy.

Graduate Training
Organic Synthesis and Materials Chemistry
Selected Publications:

B. Purushothaman, S. R. Parkin, J. E. Anthony "Synthesis and stability of soluble hexacenes" Org. Lett. 12, 2060 – 2063 (2010).

E. G. Bittle, J. W. Brill, J. E. Anthony "Electro-optic measurement of carrier mobility in an organic thin-film transistor" Appl. Phys. Lett. 97, 013302 (2010).

J. Smith, A. Bashir, G. Adamopoulos, J. E. Anthony, D. D. C. Bradley, M. Heeney, I. McCulloch, T. D. Anthopoulos "Air-stable solution-processed hybrid transistors with hole and electron mobilities exceeding 2 cm2 V-1 s-1" Adv. Mater. 22, 3598 – 3602 (2010).

J. R. Kline, S. D. Hudson, X.-R. Zhang, D. J. Gundlach, A. J. Moad, O. D. Jurchescu, T. N. Jackson, S. Subramanian, J. E. Anthony, M. F. Toney "Controlling the microstructure of solution-processable small molecules in thin film transistors through substrate chemistry" Chem. Mater. 23, 1194 – 1203 (2011)

Z. Li, Y.-F. Lim, J. B. Kim, S. R. Parkin, Y.-L. Loo, G. G. Malliaras, J. E. Anthony "Isomerically pure electron-deficient anthradithiophenes and their acceptor performance in polymer solar cells" Chem. Commun. 47, 7617 – 7619 (2011)

B. Purushothaman, M. Bruzek, S. R. Parkin, A.-F. Miller, J. E. Anthony "Synthesis and structural characterization of crystalline nonacenes" Angew. Chem. Int. Ed. 50, 7013 – 7017 (2011)

J. E. Anthony "Small-molecule, non-fullerene acceptors for polymer solar cells", invited review, Chem. Mater. 23, 583 – 590 (2011)

Y. Shu, Y.-F. Lim, Z. Li, B. Purushothaman, R. Hallani, J. E. Kim, S. R. Parkin, G. G. Malliaras, J. E. Anthony “A survey of electron-deficient pentacenes as acceptors in polymer bulk-heterojunction solar cells” Chemical Sciences 2, 363 – 366 (2011)

K. P. Goetz, Z. Li, J. W. Ward, C. Bougher, J. Rivnay, J. Smith, B. R. Conrad, S. R. Parkin, T. D. Anthopoulos, A. Salleo, J. E. Anthony, O. D. Jurchescu "Effect of acene length on electronic properties in 5-, 6-, and 7-ringed heteroacenes" Adv. Mater. 23, 3698 – 3703 (2011)

B. Purushothaman, S. R. Parkin, M. J. Kendrick, D. David, J. W. Ward, L. Yu, N. Stingelin, O. D. Jurchescu, O. Ostroverkhova, J. E. Anthony "Synthesis and charge transport studies of stable, soluble hexacenes" Chem. Commun. 48, 8261 – 8263 (2012)

O. L. Griffith, J. E. Anthony, A. G. Jones, Y. Shu, D. L. Lichtenberger "Substituent Effects on the Electronic Characteristics of Pentacene Derivatives for Organic Electronic Devices: Dioxolane-Substituted Pentacene Derivatives with Triisopropylsilylethynyl Functional Groups", J. Am. Chem. Soc. 134, 14185 - 14194 (2012)

R. Li, U. Hadayat, M. M. Payne, D.-M. Smilgies, J. E. Anthony, A. Amassian “Heterogeneous nucleation promotes carrier transport in solution-processed organic field-effect transistors” Adv. Funct. Mater. 23, 291 - 297 (2013)

H. T. Yi, M. M. Payne, J. E. Anthony, V. Podzorov "Ultra flexible solution processed organic field-effect transistors" Nature Communications. 3, 1259 – 1262 (2012)

H. U. Khan, R. P. Li, Y. Ren, L. Chen, M. M. Payne, U. S. Bhansali, D. M. Smilgies, J. E. Anthony, A. Amassian “Solvent vapor annealing in the molecular regime drastically improves carrier transport in small-molecule thin-film transistors” ACS Appl. Mater. & Interface 5, 2325 – 2330 (2013)

J. Lee, M. J. Bruzek, N. J. Thompson, M. Y. Sfeir, J. E. Anthony, M. A. Baldo “Singlet exciton fission in a hexacene derivative” Adv. Mater. 25, 1445 – 1448 (2013)

L. Y. Yu, X. R. Li, E. Pavlica, F. P. V. Koch, G. Portale, I. da Silva, M. A. Loth, J. E. Anthony, P. Smith, G. Bratina, B. K. C. Kjellander, C. W. M. Bastiaansen, D. J. Broer, G. H. Gelinck, N. Stingelin “Influence of solid-state microstructure on the electronic performance of 5,11-bis(triethylsilylethynyl)anthradithiophene” Chem. Mater. 25, 1823 – 1828 (2013)

P. J. Diemer, C. R. Lyle, Y. Mei, C. Sutton, M. M. Payne, J. E. Anthony, V. Coropceanu, J. L. Bredas, O. D. Jurchescu “Vibration-assisted crystallization improves organic / dielectric interface in organic thin film transistors” Adv. Mater. 25, 6956 – 6962 (2013)

Y. Mei, M. A. Loth, M. M. Payne, W. Zhang, J. Smith, C. S. Day, S. R. Parkin, M. Heeney, I. McCulloch, T. D. Anthopoulos, J. E. Anthony, O. D. Jurchescu “High mobility field-effect transistors with versatile processing from a small-molecule organic semiconductor” Adv. Mater. 25, 4352 – 4357 (2013)    

K. Paudel, B. Johnson, M. Thieme, M. M. Haley, M. M. Payne, J. E. Anthony, O. Ostroverkhova “Enhanced charge photogeneration promoted by crystallinity in small-molecule donor-acceptor bulk heterojunctions” Appl. Phys. Lett. 105, 043301 (2014)    

J. Anthony “Organic electronics. Addressing challenges” Nature Mater. 13, 773-775 (2014) (invited commentary)

A. Pierre, M. Sadeghi, M. M. Payne, A. Facchetti, J. E. Anthony, A. C. Arias “All-printed flexible organic transistors enabled by surface tension-guided blade coating” Adv. Mater. 26, 5722-5727 (2014)    

W. Guo, Y. Liu, W. Huang, M. M. Payne, J. Anthony, H. E. Katz “Solution-processed low-voltage organic phototransistors based on an anthradithiophene molecular solid” Org. Electron. 15, 3061 – 3069 (2014)    

M. J. Bruzek, J. E. Anthony “Synthesis and optical properties of dioxolane-functionalized hexacenes and heptacenes” Org. Lett. 16, 3608 – 3610 (2014) – Editor’s Choice  - FREE DOWNLOAD       

K. J. Thorley, J. E. Anthony “The electronic nature and reactivity of the larger acenes” Isr. J. Chem. 54, 642 – 649 (2014)    

S. L. Bayliss, A. D. Chepelianskii, A. Sepe, B. J. Walker, D. Ehrler, M. J. Bruzek, J. E. Anthony, N. C. Greenham “Geminate and nongeminate recombination of triplet excitons formed by singlet fission” Phys. Rev. Lett. 112, 238701 (2014)    

H. Zhang, Y. Yao, M. M. Payne, J. E. Anthony, J. W. Brill “Thermal diffusivities of functionalized pentacene semiconductors” Appl. Phys. Lett. 105, 073302 (2014)    

V. J. Pansare, M. J. Bruzek, D. H. Adamson, J. Anthony, R. K. Prud’homme “Composite fluorescent nanoparticles for biomedical imaging” Molecular Imaging and Biology 16, 180 – 188 (2014)    

J. W. Ward, R. Li, A. Obaid, M. M. Payne, D.-M. Smilgies, J. E. Anthony, A. Amassian, O. D. Jurchescu “Rational design of organic semiconductors for texture control and self-patterning on halogenated surfaces” Adv. Func. Mater. 24, 5168 (2014)    

C.-H. Kim, H. Hlaing, M. M. Payne, S. R. Parkin, J. E. Anthony, I. Kymissis “Difluorinated 6,13-bis(triisopropylsilylethynyl) pentacene: Synthesis, crystallinity, and charge-transport properties” ChemPhysChem in press (2015). DOI: 10.1002/cphc.201402750      

U. Kraft, J. E. Anthony, E. Ripaud, M. A. Loth, E. Weber, H. Klauk “Low-voltage organic transistors based on tetracene[2,3-b]thiophene: Contact resistance and air stability” Chem. Mater. 27, 998 – 1004 (2015)    

C.-H. Kim, H. Hlaing, J.-A. Hong, J.-H. Kim, Y. Park, M. M. Payne, J. E. Anthony, Y. Bonnassieux, G. Horowitz, I. Kymissis “Decoupling the effects of self-assembled monolayers on gold, silver, and copper organic transistor contacts” Adv. Mater. Interface 2, 384 (2015)       

M. R. Niazi, R. Li, E. Q. Li, A. R. Kirmani, M. Abdelsamie, Q. Xiao, W. Pan, M. M. Payne, J. E. Anthony, D.-M. Smilgies, S. T. Thoroddsen, E. P. Giannelis, A. Amassian “Solution-printed organic semiconductor blends exhibiting transport properties on par with single crystals” Nature Communications 6, 8598 (2015). DOI: 10.1038/ncomms9598

A. K. Hailey, S.-Y. Wang, Y. Chen, M. M. Payne, J. E. Anthony, V. Podzorov, Y.-L. Loo “Quantifying the energy barriers and elucidating the charge transport mechanisms across interspherulite boundaries in solution-processed organic semiconductor thin films” Adv. Func. Mater. 25, 5662 - 5668 (2015)

R. K. Hallani, K. J. Thorley, A. K. Hailey, S. R. Parkin, Y.-L. Loo, J. E. Anthony “The effect of regioisomerism on the crystal packing and device performance of desymmetrized anthradithiophenes” J. Mat. Chem. C 34, 8956-8962 (2015)

S. Illig, A. Eggeman, A. Troisi, L. Jiang, C. Warwick, M. Nikolka, G. Schweicher, S. Yeates, Y. Geerts, J. Anthony, H. Sirringhaus “A strategy for reducing dynamic disorder in small molecule organic semiconductors by suppressing large amplitude thermal motions” Nature Communications 7, 10736 (2016). doi:10.1038/ncomms10736

R. K. Hallani, K. J. Thorley, Y. Mei, S. R. Parkin, O. D. Jurchescu, J. E. Anthony “Structural and electronic properties of crystalline, isomerically pure anthradithiophene derivatives” Adv. Func. Mater. 26, 2341-2348 (2016).  doi:10.1002/adfm.201502440 (2016)

B. Doerling, J. D. Ryan, J. D. Craddock, A. Sorrentino, A. El Basaty, A. Gomez, M. Garriga, E. Pereiro, J. E. Anthony, M. C. Weisenberger, A. R. Goni, C. Mueller, M. Campoy-Quiles “Photoinduced p- to n-type switching in thermoelectric polymer-carbon nanotube composites” Adv. Mater. 28, 2782 – 2789 (2016)

R. D. Pensack, E. E. Ostroumov, A. J. Tilley, S. Mazza, C. Grieco, K. J. Thorley, J. B. Asbury, D. S. Seferos, J. E. Anthony, G. D. Scholes “Observation of two triplet-pair intermediates in singlet exciton fission” J. Phys. Chem. Lett. 7, 2370 – 2375 (2016)

N. M. Pinkerton, C. Froniga, V. Lobjois, B. K. Wilson, M. Bruzek, R. Prud’homme, J. E. Anthony, F. Bolze, S. Chassaing “Red-emitting EtTP-5-based organic nanoprobes for two-photon imaging in 3D multicellular biological models” RSC Advances 6, 65770 - 65774 (2016)

G.-P. Rigas, M. M. Payne, J. E. Anthony, P. Horton, F. Castro, M. Shkunov "Spray-painting of organic semiconductor single crystals", Nat. Commun. 7, 13531 (2016).  doi:10.1038/ncomms13531

D. B. Granger, Y. Mei, K. J. Thorley, S. R. Parkin, O. D. Jurchescu, J. E. Anthony “Synthesis and field effect transistor properties of derivatives of 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b’]diindolizines”, Org. Lett. 18, 6050 – 6053 (2016)

C. Grieco, G. Doucette, R. Pensack, M. Payne, A. Rimshaw, G. Scholes, J. Anthony, J. Asbury “Dynamic exchange during triplet transport in nanocrystalline TIPS-pentacene films” J. Am. Chem. Soc. 138, 16069 - 16080 (2016)

L. R. Weiss, S. L. Bayliss, F. Kraffert, K. J. Thorley, J. E. Anthony, R. Bittl, R. Friend, A. Rao, N. C. Greenham, J. Behrends “Strongly exchange-coupled triplet pairs in an organic semiconductor”  Nature Physics 13, 176 – 181 (2017)

H. L. Stern, A. Cheminal, S. R. Yost, K. Broch, S. L. Bayliss, K. Chen, M. Tabachnyk, K. Thorley, N. Greenham, J. M. Hodgkiss, J. Anthony, M. Head-Gordon, A. J. Musser, A. Rao, R. H. Friend “Vibronically coherent ultrafast triplet-pair formation and subsequent thermally deactivated dissociation control efficient endothermic singlet fission” Nature Chem. 9, 1205 (2017).

G.-P. Rigas, M. M. Payne, J. E. Anthony, P. Horton, F. Castro, M. Shkunov "Spray-painting of organic semiconductor single crystals", Nature Commun. 7, 13531 (2016).  doi:10.1038/ncomms13531

K. Wang, P. Murahari, K. Yokoyama, J. S. Lord, F. L. Pratt, J. He, L. Schulz, M. Willis, J. E. Anthony, N. A. Morley, L. Nuccio, A. Misquitta, D. J. Dunstan, K. Shimomura, I. Watanabe, S. Zhang, P. Heathcote, A. J. Drew "Temporal mapping of photochemical reactions and molecular excited states with carbon specificity", Nature Mater. 16, 467 – 471 (2017).

Y. C. Mei, P. J. Diemer, M. R. Niazi, R. K. Hallani, K. Jarolimek, C. S. Day, C. Risko, J. E. Anthony, A. Amassian, O. D. Jurchescu “Crossover from band-like to thermally activated charge transport in organic transistors due to strain-induced traps” Proc. Nat. Acad. Sci. USA 114, E6739 – E6748 (2017).

K. J. Thorley, T. W. Finn, K. Jarolimek, J. E. Anthony, C. Risko “Theory-driven insight into the crystal packing of trialkylsilylethynyl pentacenes” Chem. Mater. 29, 2502 – 2512 (2017).

C. K. Yong, A. J. Musser, S. L. Bayliss, S. Lukman, H. Tamura, O. Bubnova, R. K. Hallani, A. Meneau, R. Resel, M. Maruyama, S. Hotta, L. M. Herz, D. Beljonne, J. E. Anthony, J. Clark, H. Sirringhaus "The entangled triplet pair state in acene and heteroacene materials", Nature Commun. 8, 15953 (2017).

A. K. Hailey, A. J. Petty, J. Washbourne, K. J. Thorley, S. R. Parkin, J. E. Anthony, Y. L. Loo “Understanding the crystal packing and organic thin-film transistor performance in isomeric guest-host systems” Adv. Mater. 29, 1700048 (2017).

R. D. Pensack, C. Grieco, G. E. Purdum, S. M. Mazza, A. J. Tilley, E. E. Ostroumov, D. S. Seferos, Y. L. Loo, J. B. Asbury, J. E. Anthony, G. D. Scholes “Solution-processable, crystalline material for quantitative singlet fission” Mater. Horizons 4, 915 – 923 (2017).

A. Nunes, V. J. Pansare, N. Beziere, A. K. Ntoukas, J. Reber, M. Bruzek, J. Anthony, R. K. Prudhomme, V. Ntziachristos “Quenched hexacene optoacoustic nanoparticles” J. Mater. Chem. B 6, 44 (2018).

Q. Ai, K. Jarolimek, S. Mazza, J. E. Anthony, C. Risko “Delimited polyacenes: Edge topology as a tool to modulate carbon nanoribbon structure, conjugation, and mobility” Chem. Mater. 30, 947 (2018).

C. B. Dover, J. K. Gallaher, L. Frazer, P. C. Tapping, A. J. Petty, M. J. Crossley, J. E. Anthony, T. W. Kee, T. W. Schmidt “Endothermic singlet fission is hindered by excimer formation” Nat. Chemistry 10, 305 (2018).

D. M. Kroupa, D. H. Arias, J. L. Blackburn, G. M. Carroll, D. B. Granger, J. E. Anthony, M. C. Beard, J. C. Johnson “Control of energy flow dynamics between tetracene ligands and PbS quantum dots by size tuning and ligand coverage” Nano Lett. 18, 865 (2018).

A. Abtahi, S. M. Mazza, S. M. Ryno, E. K. Loya, R. Li, S. R. Parkin, C. Risko, J. E. Anthony, K. R. Graham “Effect of halogenation on the energetics of pure and mixed phases in model organic semiconductors composed of anthradithiophene derivatives and C60” J. Phys. Chem. C 122, 4757 (2018).

N. A. Pace, D. H. Arias, D. B. Granger, S. Christensen, J. E. Anthony, J. C. Johnson “Dynamics of singlet fission and electron injection in self-assembled acene monolayers on titanium dioxide” Chem. Sci. (in press 2018).