Unconventional, Chemically Stable, and Soluble Two-Dimensional Angular Polycyclic Aromatic Hydrocarbons: From Molecular Design to Device Applications

Accounts of Chemical Research

Volumn 48, Issue 3, 2015, Pages 500-509

  Zhang, Lei ^a   Cao, Yang ^b   Colella, Nicholas S ^a   Liang, Yong ^b   Brédas, Jean Luc ^d   Houk, K N ^b,c   Briseno, Alejandro L ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c Engineering IV   (United States)

^d KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84925447060     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500278w     Document Type: Article

References (51)

1. Clar, E. The Aromatic Sextet; Wiley-VCH: London, 1972.
2. Haley, M. M., Tykwinski, R. R., Eds. Carbon-Rich Compounds: From Molecules to Materials; Wiley-VCH: Weinheim, 2006.
3. Wu, J.; Pisula, W.; Müllen, K. Graphenes as Potential Material for Electronics Chem. Rev. 2007, 107, 718-747
4. Bendikov, M.; Wudl, F.; Perepichka, D. F. Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics Chem. Rev. 2004, 104, 4891-4946
5. Anthony, J. E. Functionalized Acenes and Heteroacenes for Organic Electronics Chem. Rev. 2006, 106, 5028-5048
6. Anthony, J. E. The Larger Acenes: Versatile Organic Semiconductors Angew. Chem., Int. Ed 2008, 47, 452-483
7. Wei, J.; Yan, L.; Wang, Z. Heteroarenes as high performance organic semiconductors Chem. Soc. Rev. 2013, 42, 6113-6127
8. Takimiya, K.; Osaka, I.; Mori, T.; Nakano, M. Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure Acc. Chem. Res. 2014, 47, 1493-1502
9. Zade, S. S.; Bendikov, M. Heptacene and Beyond: The Longest Characterized Acenes Angew. Chem. Int. Ed 2010, 49, 4012-4015
10. Biermann, D.; Schmidt, W. Diels-Alder Reactivity of Polycyclic Aromatic Hydrocarbons. 1. Acenes and Benzologs J. Am. Chem. Soc. 1980, 102, 3163-3173
11. Havey, R. G. Polycyclic Aromatic hydrocarbons; Wiley-VCH: New York, 1997.
12. Schleyer, P. V. R.; Manoharan, M.; Jiao, H.; Stahl, F. The Acenes: Is There a Relationship between Aromatic Stabilization and Reactivity? Org. Lett. 2001, 3, 3643-3646
13. Ehrlich, S.; Bettinger, H. F.; Grimme, S. Dispersion-Driven Conformational Isomerism in σ-Bonded Dimers of Larger Acenes Angew. Chem., Int. Ed 2013, 52, 10892-10895
14. Einholz, R.; Bettinger, H. F. Heptacene: Increased Persistence of a 4n+2 π-Electron Polycyclic Aromatic Hydrocarbon by Oxidation to the 4n π-Electron Dication Angew. Chem., Int. Ed 2013, 52, 9818-9820
15. Zade, S. S.; Zamoshchik, N.; Reddy, A. R.; Marueli, G. F.; Sheberla, D.; Bendikov, M. Products and Mechanism of Acene Dimerization. A Computational Study J. Am. Chem. Soc. 2011, 133, 10803-10806
16. Xiao, J.; Duong, H.; Liu, Y.; Shi, W.; Ji, L.; Li, G.; Li, S.; Liu, X.; Ma, J.; Wudl, F.; Zhang, Q. Synthesis and Structure Characterization of a Stable Nonatwistacene Angew. Chem., Int. Ed 2012, 51, 6094-6098
17. Purushothaman, B.; Bruzek, M.; Parkin, S. R.; Miller, A.; Anthony, J. E. Synthesis and Structural Characterization of Crystalline Nonacenes Angew. Chem., Int. Ed 2011, 50, 7013-7017
18. Kaur, I.; Jazdzyk, M.; Stein, N. N.; Prusevich, P.; Miller, G. P. Design, Synthesis, and Characterization of a Persistent Nonacene Derivative J. Am. Chem. Soc. 2010, 132, 1261-1263
19. Chun, D.; Cheng, Y.; Wudl, F. The Most Stable and Fully Characterized Functionalized Heptacene Angew. Chem., Int. Ed 2008, 47, 8380-8385
20. Payne, M. M.; Parkin, S. R.; Anthony, J. E. Functionalized Higher Acenes: Hexacene and Heptacene J. Am. Chem. Soc. 2005, 127, 8028-8029
21. Debije, M. G.; Piris, D.; de Haas, M. P.; Warman, J. M.; Tomović, Z.; Simpson, C. D.; Watson, M. D.; Müllen, K. The Optical and Charge Transport Properties of Discotic Materials with Large Aromatic Hydrocarbon Cores J. Am. Chem. Soc. 2004, 126, 4641-4645
22. Clar, E. Polycyclic Hydrocarbons; Academic Press: New York, 1964; Vol. 1.
23. Suresh, C. H.; Gadre, S. R. Clar's Aromatic Sextet Theory Revisited via Molecular Electrostatic Potential Topography J. Org. Chem. 1999, 64, 2505-2512
24. Pérez, D.; Peña, D.; Guitián, E. Aryne Cycloaddition Reactions in the Synthesis of Large Polycyclic Aromatic Compounds Eur. J. Org. Chem. 2013, 5981-6013
25. Chen, L.; Hernandez, Y.; Feng, X.; Müllen, K. From Nanographene and Graphene Nanoribbons to Graphene Sheets: Chemical Synthesis Angew. Chem., Int. Ed 2012, 51, 7640-7654
26. Fudickar, W.; Linker, T. Why Triple Bonds Protect Acenes from Oxidation and Decomposition J. Am. Chem. Soc. 2012, 134, 15071-15082
27. Northrop, B. H.; Houk, K. N.; Maliakal, A. Photostability of Pentacene and 6,13-Disubstituted Pentacene Derivatives: A Theoretical and Experimental Mechanistic Study Photochem. Photobiol. Sci. 2008, 7, 1463-1468
28. Tsefrikas, V. M.; Scott, L. T. Geodesic Polyarenes by Flash Vacuum Pyrolysis Chem. Rev. 2006, 106, 4868-4884
29. Yang, C.; Harvey, R. G. Synthesis of Methylene-Bridged Polycyclic Aromatic Hydrocarbons J. Org. Chem. 1993, 58, 4155-4158
30. Zhang, X.; Li, J.; Qu, H.; Chi, C.; Wu, J. Fused Bispentacenequinone and Its Unexpected Michael Addition Org. Lett. 2010, 12, 3946-3949
31. Zhang, L.; Fonari, A.; liu, Y.; Hoyt, A.; Lee, H.; Granger, D.; Parkin, S.; Russell, T. P.; Anthony, J. E.; Brédas, J. L.; Coropceanu, V.; Briseno, A. L. Bistetracene: An Air-Stable, High-Mobility Organic Semiconductor with Extended Conjugation J. Am. Chem. Soc. 2014, 136, 9248-9251
32. Wiberg, K. B. Properties of Some Condensed Aromatic Systems J. Org. Chem. 1997, 62, 5720-5727
33. Purushothaman, B.; Parkin, S. R.; Anthony, J. E. Synthesis and Stability of Soluble Hexacenes Org. Lett. 2010, 12, 2060-2063
34. Zhang, L.; Fonari, A.; Zhang, Y.; Zhao, G.; Coropceanu, V.; Hu, W.; Parkin, S.; Brédas, J. L.; Briseno, A. L. Triisopropylsilylethynyl-Functionalized Graphene-Like Fragment Semiconductors: Synthesis, Crystal Packing, and Density Functional Theory Calculations Chem.-Eur. J. 2013, 19, 17907-17916
35. Miller, G. P.; Mack, J. Completely Regioselective, Highly Stereoselective Syntheses of cis-Bisfullerene[60] Adducts of 6,13-Disubstituted Pentacenes Org. Lett. 2000, 2, 3979-3982
36. Lloyd, M. T.; Anthony, J. E.; Malliaras, G. G. Photovoltaics from Soluble Small Molecules Mater. Today 2007, 10, 34-41
37. Cao, Y.; Liang, Y.; Zhang, L.; Osuna, S.; Hoyt, A-L. M.; Briseno, A. L.; Houk, K. N. Why Bistetracenes Are Much Less Reactive than Pentacenes in Diels-Alder Reactions with Fullerenes J. Am. Chem. Soc. 2014, 136, 10743-10751
38. Desiraju, G. R.; Gavezzotti, A. A Systematic Analysis of Packing Energies and Other Packing Parameters for Fused-Ring Aromatic Hydrocarbons Acta Crystallogr. B 1988, 44, 427-434
39. 2-Coordination Inorg. Chem. 2001, 40, 3191-3199
40. Sherrill, C. D. Energy Component Analysis of π Interactions Acc. Chem. Res. 2013, 46, 1020-1028
41. Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Organic Semiconductors: A Theoretical Characterization of the Basic Parameters Governing Charge Transport Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804-5809
42. Burke, K. B.; Shu, Y.; Kemppinen, P.; Singh, B.; Bown, M.; Liaw, I. I.; Williamson, R. M.; Thomsen, L.; Dastoor, P.; Belcher, W.; Forsyth, C.; Winzenberg, K. N.; Collis, G. E. Single Crystal X-ray, AFM, NEXAFS, and OFET Studies on Angular Polycyclic Aromatic Silyl-Capped 7,14-Bis(ethynyl)dibenzo[b,def ]chrysenes Cryst. Growth Des 2012, 12, 725-731
43. Shu, Y.; Collis, G. E.; Dunn, C. J.; Kemppinen, P.; Winzenberg, K. N.; Williamson, R. M.; Bilic, A.; Birendra Singh, T.; Bown, M.; McNeillc, C. R.; Thomsenb, L. The impact of Tetrahedral Capping Groups and Device Processing Conditions on the Crystal Packing, Thin Film Features and OFET Hole Mobility of 7,14-Bis(ethynyl)-dibenzo[ b, def ]chrysenes J. Mater. Chem. C 2013, 1, 6299-6307
44. Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J. L. Charge Transport in Organic Semiconductors Chem. Rev. 2007, 107, 926-952
45. Goldman, C.; Haas, S.; Krellner, C.; Pernstich, P.; Gundlach, D. J.; Batlogg, B. Hole Mobility in Organic Single Crystals Measured by a "Flip-Crystal" Field-Effect Technique J. Appl. Phys. 2004, 96, 2080-2086
46. Watanabe, M.; Chang, Y.; Liu, S.; Chao, T.; Goto, K.; Minarul Islam, M.; Yuan, C.; Tao, Y.; Shinmyozu, T.; Chow, T. J. The synthesis, Crystal Structure and Chargetransport Properties of Hexacene Nat. Chem. 2012, 4, 575-578
47. Winzenberg, K. N.; Kemppinen, P.; Fanchini, G.; Bown, M.; Collis, G. E.; Forsyth, C. M.; Hegedus, K.; Singh, Th. B.; Watkins, S. E. Dibenzo[b,def]chrysene Derivatives: Solution-Processable Small Molecules that Deliver High Power-Conversion Efficiencies in Bulk Heterojunction Solar Cells Chem. Mater. 2009, 21, 5701-5703
48. Scholes, F. H.; Ehlig, T.; James, M.; Lee, K. H.; Duffy, N.; Scully, A. D.; Singh, T. B.; Winzenberg, K. N.; Kemppinen, P.; Watkins, S. E. Intraphase Microstructure-Understanding the Impact on Organic Solar Cell Performance Adv. Funct. Mater. 2013, 23, 5655-5662
49. Zhang, L.; Walker, B.; Liu, F.; Colella, N. S.; Mannsfeld, S. C. B.; Watkins, J. J.; Nguyen, T.-Q.; Briseno, A. L. Triisopropylsilylethynyl-Functionalized Dibenzo[ def, mno ]chrysene: A Solution-Processed Small Molecule for Bulk Heterojunction Solar Cells J. Mater. Chem. 2012, 22, 4266-4268
50. Walker, B.; Kim, C.; Nguyen, T.-Q. Small Molecule Solution-Processed Bulk Heterojunction Solar Cells Chem. Mater. 2011, 23, 470-482
51. Liu, F.; Zhang, L.; Zhang, Y.; Mannsfeld, S. C. B.; Russell, T. P.; Briseno, A. L. Interpenetrating Morphology based on Highly Crystalline Small Molecule and PCBM Blends J. Mater. Chem. C 2014, 2, 9368-9374