Electrogenerated chemiluminescence of bithiophenes with methylthio functionalities

Journal of Physical Chemistry C

Volumn 118, Issue 2, 2014, Pages 924-932

  Ritzert, Nicole L ^a   Truong, Thanh Tam ^a   Coates, Geoffrey W ^a   Abruña, Héctor D ^a  

^a Cornell University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SIDE CHAINS; ELECTROGENERATED CHEMILUMINESCENCE; FLUORESCENCE QUANTUM YIELD; IRREVERSIBLE REDUCTION; NEGATIVE POTENTIAL; SOLVENT STABILITY; TETRA-HYDROFURAN; TWO-ELECTRON OXIDATION PROCESS;

ACETONITRILE; BENZOYL PEROXIDE; CHEMILUMINESCENCE; CRYSTAL DEFECTS;

ORGANIC SOLVENTS;

EID: 84892778772     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp412100x     Document Type: Article

References (58)

1. Bard, A. J. Integrated Chemical Systems: A Chemical Approach to Nanotechnology; Wiley: New York, 1994.
2. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Electroluminescence in Conjugated Polymers Nature 1999, 397, 121-128
3. Fichou, D. Structural Order in Conjugated Oligothiophenes and Its Implications on Opto-Electronic Devices J. Mater. Chem. 2000, 10, 571-588
4. Mishra, A.; Ma, C.-Q.; Bäuerle, P. Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications Chem. Rev. 2009, 109, 1141-1276
5. Pron, A.; Gawrys, P.; Zagorska, M.; Djurado, D.; Demadrille, R. Electroactive Materials for Organic Electronics: Preparation Strategies, Structural Aspects, and Characterization Techniques Chem. Soc. Rev. 2010, 39, 2577-2632
6. Cutler, C. A.; Burrell, A. K.; Officer, D. L.; Too, C. O.; Wallace, G. G. Effect of Electron Withdrawing or Donating Substituents on The Photovoltaic Performance of Polythiophenes Synth. Met. 2002, 128, 35-42
7. Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S. I.; Marks, T. J. A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells J. Am. Chem. Soc. 2011, 133, 8142-8145
8. Huang, J.; Luo, H.; Wang, L.; Guo, Y.; Zhang, W.; Chen, H.; Zhu, M.; Liu, Y.; Yu, G. Dibenzoannelated Tetrathienoacene: Synthesis, Characterization, and Applications in Organic Field-Effect Transistors Org. Lett. 2012, 14, 3300-3303
9. Mallet, C.; Didane, Y.; Watanabe, T.; Yoshimoto, N.; Allain, M.; Videlot-Ackermann, C.; Frère, P. Electronic Properties and Field-Effect Transistors of Oligomers End-Capped with Benzofuran Moieties ChemPlusChem 2013, 78, 459-466
10. Mitschke, U.; Bäuerle, P. Synthesis, Characterization, and Electrogenerated Chemiluminescence of Phenyl-Substituted, Phenyl-Annulated, and Spirofluorenyl-Bridged Oligothiophenes J. Chem. Soc., Perkin Trans. 1 2001, 740-753
11. Henderson, J. C.; Kiya, Y.; Hutchison, G. R.; Abruña, H. D. 5,5′-Bis(methylthio)-2,2′-bithiophene: A Potential Cathode Electroactive Material for Energy Storage Devices J. Phys. Chem. C 2008, 112, 3989-3997
12. Burkhardt, S. E.; Lowe, M. A.; Conte, S.; Qian, H.; Zhou, W.; Rodriguez-Calero, G. G.; Gao, J.; Hennig, R. G.; Abruña, H. D. Tailored Redox Functionality of Small Organics for Pseudocapacitive Electrodes Energy Environ. Sci. 2012, 5, 7176-7187
13. Burkhardt, S. E.; Conte, S.; Rodriguez-Calero, G. G.; Lowe, M. A.; Qian, H.; Zhou, W.; Gao, J.; Hennig, R. G.; Abruña, H. D. Towards Organic Energy Storage: Characterization of 2,5-Bis(methylthio)thieno[3,2-b]thiophene J. Mater. Chem. 2011, 21, 9553-9563
14. Dell, E. J.; Capozzi, B.; DuBay, K. H.; Berkelbach, T. C.; Moreno, J. R.; Reichman, D. R.; Venkataraman, L.; Campos, L. M. Impact of Molecular Symmetry on Single-Molecule Conductance J. Am. Chem. Soc. 2013, 135, 11724-11727
15. Hicks, R. G.; Nodwell, M. B. Synthesis and Electronic Structure Investigations of α,ω-Bis(arylthiol)oligothiophenes: Towards Understanding Wire-Linker Interactions in Molecular-Scale Electronic Materials J. Am. Chem. Soc. 2000, 122, 6746-6753
16. Guay, J.; Kasai, D.; Diaz, A.; Wu, R.; Tour, J. M.; Dao, L. H. Chain-Length Dependence of Electrochemical and Electronic Properties of Neutral and Oxidized Soluble α,α-Coupled Thiophene Oligomers Chem. Mater. 1992, 4, 1097-1105
17. Nepomnyashchii, A. B; Ono, R. J.; Lyons, D. M.; Sessler, J. L.; Bielawski, C. W.; Bard, A. J. Oligothiophene Nanoparticles: Photophysical and Electrogenerated Chemiluminescence Studies J. Phys. Chem. Lett. 2012, 3, 2035-2038
18. Kurach, E.; Kotwica, K.; Zapala, J.; Knor, M.; Nowakoski, R.; Djurado, D.; Toman, P.; Pfleger, J.; Zagorska, M.; Pron, A. Semiconducting Alkyl Derivatives of 2,5(Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole-Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties J. Phys. Chem. C 2013, 117, 15316-15326
19. van Hutten, P. F.; Gill, R. E.; Herrema, J. K.; Hadziiannou, G. Structure of Thiophene-Based Regioregular Polymers and Block Copolymers and Its Influence on Luminescence Spectra J. Phys. Chem. 1995, 99, 3218-3224
20. Nepomnyashchii, A. B.; Ono, R. J.; Lyons, D. M.; Bielawski, C. W.; Sessler, J. L.; Bard, A. J. Electrochemistry and Electrogenerated Chemiluminescence of Thiophene and Fluorene Oligomers. Benzoyl Peroxide as a Coreactant for Oligomerization of Thiophene Dimers Chem. Sci. 2012, 3, 2628-2638
21. Hill, M. G.; Mann, K. R.; Miller, L. L.; Penneau, J.-F. Oligothiophene Cation Radical Dimers. An Alternative to Bipolarons in Oxidized Polythiophene J. Am. Chem. Soc. 1992, 114, 2728-2730
22. Hill, M. G.; Penneau, J.-F.; Zinger, B.; Mann, K. R.; Miller, L. L. Oligothiophene Cation Radicals. π-Dimers as Alternatives to Bipolarons in Oxidized Polythiophenes Chem. Mater. 1992, 4, 1106-1113
23. Bäuerle, P. End-Capped Oligothiophenes-New Model Compounds for Polythiophenes Adv. Mater. 1992, 4, 102-107
24. Lee, K.-H.; Ohshita, J.; Kunai, A. Synthesis and Properties of Bis(methylthio)dithienosilole and Its Oxides Organometallics 2004, 23, 5481-5487
25. Libert, M.; Bard, A. J. Electrogenerated Chemiluminescence. XXVI. Systems Involving Tetraarylpyrroles, Tetraphenylfuran, and Tetraphenylthiophene J. Electrochem. Soc. 1976, 123, 814-818
26. Booker, C.; Wang, X.; Haroun, S.; Zhou, J.; Jennings, M.; Pagenkopf, B. L.; Ding, Z. Tuning of Electrogenerated Silole Chemiluminescence Angew. Chem., Int. Ed. 2008, 47, 7731-7735
27. Shen, M.; Rodríguez-López, J.; Huang, J.; Liu, Q.; Zhu, X.-H.; Bard, A. J. Electrochemistry and Electrogenerated Chemiluminescence of Dithienylbenzothiadiazole Derivative. Differential Reactivity of Donor and Acceptor Groups and Simulations of Radical Cation-Anion and Dication-Radical Anion Annihilations J. Am. Chem. Soc. 2010, 132, 13453-13461
28. Bard, A. J., Ed. Electrogenerated Chemiluminescence; Marcel Dekker: New York, 2004.
29. Richter, M. M. Electrochemiluminescence (ECL) Chem. Rev. 2004, 104, 3003-3036
30. Miao, W. Electrogenerated Chemiluminescence. In Handbook of Electrochemistry; Zoski, C. G., Ed. Elsevier: Oxford, UK, 2007, pp 541-590.
31. Forster, R. J.; Bertoncello, P.; Keyes, T. E. Electrogenerated Chemiluminescence. Annu Rev. Anal. Chem. 2009, 2, 59-85
32. Chandross, E. A.; Sonntag, F. I. Chemiluminescent Electron-Transfer Reactions of Radical Anions J. Am. Chem. Soc. 1966, 88, 1089-1096
33. Akins, D. L.; Birke, R. L. Energy Transfer in Reactions of Electrogenerated Aromatic Anions and Benzoyl Peroxide. Chemiluminescence and Its Mechanism Chem. Phys. Lett. 1974, 29, 428-435
34. Santa Cruz, T. D.; Akins, D. L.; Birke, R. L. Chemiluminescence and Energy Transfer in Systems of Electrogenerated Aromatic Anions and Benzoyl Peroxide J. Am. Chem. Soc. 1976, 98, 1677-1682
35. Ellinger, S.; Kreyes, A.; Zeiner, U.; Hoffmann-Richter, C.; Landfester, K.; Möller, M. Aggregation Phenomena of Long α-and α,ω-Substituted Oligothiophenes-the Effect of Branched vs. Linear End-Groups Eur. J. Org. Chem. 2007, 5686-5702
36. Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. Indium-Catalyzed Annulation of 2-Aryl-and 2-Heteroarylindoles with Propargyl Ethers: Concise Synthesis and Photophysical Properties of Diverse Aryl-and Heteroaryl-Annulated[a]carbazoles J. Am. Chem. Soc. 2008, 130, 15823-15835
37. Brouwer, A. M. Standards for Photoluminescence Quantum Yield Measurements in Solution (IUPAC Technical Report) Pure Appl. Chem. 2011, 83, 2213-2228
38. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2 nd ed.; Kluwer Academic/Plenum: New York, 1999; pp 25-61.
39. Suzuki, K.; Kobayashi, A.; Kaneko, S.; Takehira, K.; Yoshihara, T.; Ishida, H.; Shiina, Y.; Oishi, S.; Tobita, S. Reevaluation of Absolute Luminescence Quantum Yields of Standard Solutions using a Spectrometer with an Integrating Sphere and a Back-thinned CCD Detector Phys. Chem. Chem. Phys. 2009, 11, 9850-9860
40. Hamai, S.; Hirayama, F. Actinometric Determination of Absolute Fluorescence Quantum Yields J. Phys. Chem. 1983, 87, 83-89
41. Bard, A. J.; Fan, F.-R. F.; Mirkin, M. V. Scanning Electrochemical Microscopy. In Electroanalytical Chemistry: A Series of Advances; Bard, A. J., Ed.; Marcel Dekker: New York, 1994; Vol. 18, pp 243-373.
42. Sahami, S.; Weaver, M. J. Entropic and Enthalpic Contributions to the Solvent Dependence of the Thermodynamics of Transition-Metal Redox Couples: Part II. Couples Containing Ammine and Ethylenediamine Ligands J. Electroanal. Chem. 1981, 122, 171-181
43. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2 nd ed.; Wiley: New York, 2001.
44. Harris, D. C.; Bertolucci, M. D. Symmetry and Spectroscopy. An Introduction to Vibrational and Electronic Spectroscopy; Dover: New York, 1989.
45. Atkins, P.; de Paula, J. Physical Chemistry, 8 th ed.; W. H. Freeman and Co.: New York, 2006; Vol. 2, pp 39, 155-156.
46. Miller, L. L.; Yu, Y. Synthesis of β-Methoxy, Methyl-Capped α-Oligophenes J. Org. Chem. 1995, 60, 6813-6819
47. Neudeck, A.; Audebert, P.; Guyard, L.; Dunsch, L.; Guiriec, P.; Hapiot, P. π-Dimer from Bithiophene Radical Cations. Investigation of Equilibrium Constants as a Function of Substituent Size and Supporting Electrolyte Using Fast Conversion Electrochemical Cells Acta Chem. Scand. 1999, 53, 867-875
48. Nicholson, R. S.; Shain, I. Theory of Stationary Electrode Polarography: Single Scan and Cyclic Methods Applied to Reversible, Irreversible, and Kinetic Systems Anal. Chem. 1964, 36, 706-723
49. Engelmann, G.; Kossmehl, G.; Heinze, J.; Tschunsky, P.; Jugut, W.; Welzel, H.-P. Studies on β-Methylated End-Capped Bithiophenes J. Chem. Soc., Perkin Trans. 2 1998, 169-175
50. Cruser, S. A.; Bard, A. J. Electrogenerated Chemiluminescence. III. Intensity-Time and Concentration-Intensity Relationships and the Lifetime of Radical Cations of Aromatic Hydrocarbons in N,N-Dimethylformamide Solution J. Am. Chem. Soc. 1969, 91, 267-275
51. 8amide: A BODIPY-Based Molecule with Asymmetric Transients J. Phys. Chem. C 2008, 112, 10833-10841
52. Weller, A.; Zachariasse, K. Chemiluminescence from Chemical Oxidation of Aromatic Anions J. Chem. Phys. 1967, 46, 4984-4985
53. Faulkner, L. R.; Tachikawa, H.; Bard, A. J. Electrogenerated Chemiluminescence. VII. The Influence of an External Magnetic Field on Luminescence Intensity J. Am. Chem. Soc. 1972, 94, 691-699
54. Visco, R. E.; Chandross, E. A. On the Mechanism of the Electrochemiluminescence of Aromatic Hydrocarbons in Aprotic Solvents Electrochim. Acta 1968, 13, 1187-1196
55. Choi, J.-P.; Wong, K.-T.; Chen, Y.-M.; Yu, Y.-K.; Chou, P.-T.; Bard, A. J. Electrogenerated Chemiluminescence. 76. Excited State Emission vs Excimer Emission in Ter(9,9-diarylfluorenes) J. Phys. Chem. B 2003, 107, 14407-14413
56. Nepomnyashchii, A. B; Bröring, M.; Ahrens, J.; Bard, A. J. Chemical and Electrochemical Detection of BODIPY Compounds: Electrogenerated Chemiluminescent Detection of Dimer Formation J. Am. Chem. Soc. 2011, 133, 19498-19504
57. Fleet, B.; Kirkbright, G. F.; Pickford, C. J. The Electrogenerated Chemiluminescence of Pyrene and Some Related Compounds J. Electroanal. Chem. 1971, 30, 155-121
58. Suk, J.; Wu, Z.; Wang, L.; Bard, A. J. Electrochemistry, Electrogenerated Chemiluminescence, and Excimer Formation Dynamics of Intramolecular π-Stacked 9-Naphthylanthracene Derivatives and Organic Nanoparticles J. Am. Chem. Soc. 2011, 133, 14675-14685