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Michael Haley

  • Title: Professor
  • Additional Title: Organic, Organometallic, & Materials Chemistry; Richard M. & Patricia H. Noyes Professor
  • Phone: (541) 346-0456
  • Office: 385 Onyx Bridge
  • Affiliated Departments: Materials Science Institute
  • Website: Website

Education

B.A., Rice University, 1987. Ph.D., Rice University, 1991 (W. Edward Billups). Postdoctoral: University of California, Berkeley, 1991-93 (K. Peter C. Vollhardt). Honors and Awards: American Chemical Society, Division of Organic Chemistry Fellowship, 1990-91; NSF Postdoctoral Fellowship, 1991-93; NSF CAREER Award, 1995-1998; US-Israel BSF Ernst D. Bergmann Memorial Award, 1997; Richard A. Bray Faculty Fellow, 1998; Camille Dreyfus Teacher-Scholar, 1998-2003; Alexander von Humboldt Research Fellow, 2000-2001; Thomas F. Herman Faculty Achievement Award for Distinguished Teaching, 2002; University of Oregon Fund for Faculty Members Excellence Award, 2007; Fellow, American Association for the Advancement of Science, 2011. At Oregon since 1993.

Research

The research interests of my group are deeply rooted in the exploration of important non-natural pi-electron rich systems. The group utilizes current synthetic methodology for the preparation of novel organic materials and compounds of theoretical interest. We investigate these compounds by modern physical organic methods to determine the important physical and chemical properties of these systems, such as conductivity, absorption/emission behavior, through-bond and through-space electronic interactions. Graduate and undergraduate students are actively involved in all aspects of the research, thus acquiring a strong synthetic and theoretical background.

1. Organic Semiconductors

Polycyclic hydrocarbons that possess extended pi-conjugation are of tremendous interest because of their potential use in optical and electronic device applications. While a majority of studies have focused on acenes and their derivatives, these systems are susceptible to oxidative and photolytic degradation; thus, there is a pressing need for alternative, acene-like topologies. Current research in the lab is focused on molecules based on or inspired by the indenofluorene (IF) skeleton, such as compounds 1-5 (Figure 1). Over the last few years, we have adapted and/or developed general methods for the assembly of a variety of fully conjugated IF derivatives and initiated exploration of their materials properties. We have shown that IFs can be prepared gram quantities in good overall yields and in excellent purity. In addition to being challenging synthetic targets, indenofluorenes are providing fundamental answers about structure, bonding, and reactivity in expanded, conjugated structures, and have the potential to act as rigid, planar, electron-accepting cores for the formation of advanced materials with novel electronic properties. We are exploiting the materials potential of IFs via a combined experimental and theoretical approach, with an emphasis towards use of indenofluorenes as organic semiconductors in devices. Importantly, we demonstrated recently that single crystals of IF 3 could serve as an active layer in an organic field-effect transistor that exhibits ambipolar behavior.

Figure1

Figure 1. Indenofluorene and indenofluorene-inspired structures 1-5.

2. Supramolecular Chemistry of Arylethynyl Scaffolding

Anions are problematic environmental contaminants and are vital to many processes in nature, with anion binding proteins and transport channels implicated in the mechanisms of many disease pathways. This avenue of research is a productive collaboration between the Haley lab and that of UO colleague Darren Johnson to target new organic receptors that selectively bind and sense anions. The project is a union of the synthetic expertise of the Haley group to assemble relatively rigid and inherently fluorescent molecules based on arylethynyl scaffolding with the extensive knowledge of the Johnson lab to design and exhaustively analyze complex supramolecular systems. Molecules 6-8 are representative receptors (Figure 2). The modularity of our design strategy allows for exploration of a variety of recognition motifs for anions, including electrostatic attractions, hydrogen bond interactions and attractions with electron-deficient arenes (anion-pi, CH•••X– hydrogen bonds and weak-sigma complexes). This flexibility affords the possibility of selectively binding anions that are challenging to target with traditional approaches. Core and linker substitution provides another approach to tuning the selectivity of the receptors by changing the shape and size of the binding pocket. The functionality of the receptors can also be adjusted to provide a route to make the molecules water-soluble or even permeable to cell membranes. These molecules will have long-term applications in sensing, imaging and/or remediating anions, which will impact public health in both discovering and removing environmental contaminants and imaging the role anions play in biological processes.

Figure 2. Representative examples of completed arylethyl receptors.

3. Myotonic Dystrophy Therapeutics

In a close collaboration with UO biochemist Andy Berglund and his lab, we are developing therapeutics for Myotonic Dystrophy (DM). DM is the most common form of adult onset muscular dystrophy affecting 1 in 8000 people. DM is caused by an expansion of three or four nucleotide repeats–CUG in patients with myotonic dystrophy type I (DM1), and CCUG expansions in patients with myotonic dystrophy type 2 (DM2). Both DM1 and DM2 patients display many of the same symptoms (myotonia, progressive muscle weakness and wasting, cataracts, cardiac and developmental defects) strongly suggesting that both DM1 and DM2 work through the same or very similar mechanisms. In 2007 the Berglund lab discovered that pentamidine (9) as a molecule that binds CUG repeats and reverses some of the molecular defects of DM. We are preparing a wide variety of simple (e.g., 10, 11) and more complex pentamidine analogues for determining structure-activity relationships to improve their efficacy over 9 and thus potentially generate a therapeutic for DM.

Figure 3. Pentamidine 9 and structural analogues 10 and 11.

The work described on this web page has been generously supported by The National Science Foundation with additional contributions from The Petroleum Research Fund, The Camille and Henry Dreyfus Foundation, The Alexander von Humboldt Foundation and the Oregon Nanosciences and Microtechnologies Institute.

 

Publications

“Electron-Accepting 6,12-Diethynylindeno[1,2-b]fluorenes: Synthesis, Crystal Structures, & Photophysical Properties.” D. T. Chase, A. G. Fix, B. D. Rose, C. D. Weber, S. Nobusue, C. E. Stockwell, L. N. Zakharov, M. C. Lonergan and M. M. Haley, Angew. Chem. Int. Ed. 2011, 50, 11103-11106.

“6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics and Ambipolar OFETs.” D. T. Chase, A. G. Fix, S. J. Kang, B. D. Rose, C. D. Weber, Y. Zhong, L. N. Zakharov, M. C. Lonergan, C. Nuckolls and M. M. Haley, J. Am. Chem. Soc. 2012, 134, 10349-10352.

“Fluoreno[4,3-c]fluorene: A Closed-Shell, Fully-Conjugated Hydrocarbon.” B. D. Rose, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Org. Lett. 2012, 14, 2426-2429.

“Arylethynyl Receptors for Anions and Emerging Applications in Cellular Imaging.” C. N. Carroll, J. J. Naleway, M. M. Haley and D. W. Johnson, Chem. Soc. Rev. 2010, 39, 3875-3888.

“Anion-Dependent Fluorescence in Bis(anilinoethynyl)pyridine Derivatives: Switchable ON-OFF and OFF-ON Responses.” C. N. Carroll, B. A. Coombs, S. P. McClintock, C. A. Johnson II, O. B. Berryman, D. W. Johnson, and M. M. Haley, Chem. Commun. 2011, 47, 5539-5541.

“Synthesis and Optoelectronic Properties of 2,6-Bis(2-anilinoethynyl)pyridine Scaffolds.” J. M. Engle, C. N. Carroll, D. W. Johnson and M. M. Haley, Chem. Sci. 2012, 3, 1105-1110.

Additional Publications (since 2005)

Note: Names in green = grad students, names in blue = undergraduates.

73. "Structure-Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes." J. A. Marsden, J. J. Miller, L. D. Shirtcliff, and M. M. Haley, J. Am. Chem. Soc. 2005, 127, 2464-2476.

74. "Selective Metallacyclization and Crystallographic Characterization of a Family of Platina-annulenes." C. A. Johnson II, M. M. Haley, E. Rather, F. Han, and T. J. R. Weakley, Organometallics 2005, 24, 1161-1172.

75. "Carbon Networks Based on Dehydrobenzoannulenes. 5. Extension of Two-Dimensional Conjugation in Graphdiyne Nanoarchitectures." J. A. Marsden and M. M. Haley, J. Org. Chem. 2005, 70, 10213-10226 (cover of journal).

76. "[2.2]Paracyclophane/Dehydroannulene Hybrids: Probing the Aromaticity of the Dehydro[14]annulene Framework." H. Hinrichs, A.K. Fischer, P.G. Jones, H. Hopf, and M.M. Haley, Org Lett. 2005, 7, 3793-3795.

77. "The Effects of Donor-Acceptor Substitution Symmetry on the Nonlinear Absorption of Two-Dimensionally-Conjugated Isomeric Chromophores." A. Slepkov, J. A. Marsden, J. J. Miller, L. D. Shirtcliff, M. M. Haley, K. Kamada, R. R. Tykwinski, and F. A. Hegmann, Proc. SPIE 2005, 5934, 29-34.

78. "Optical Excitations in Carbon Architectures Based on Dodecadehydrotribenzo[18]annulene." S. Anand, O. Varnavski, J. A. Marsden, M. M. Haley, H. B. Schlegel, and T. Goodson III, J. Phys. Chem. A 2006, 111, 1305-1318.

79. "Synthesis and Characterization of Pyridine- and Thiophene-based Platinacyclyne Topologies." C. A. Johnson II, B. A. Baker, O. B. Berryman, L. N. Zakharov, M. J. O'Connor, and M. M. Haley, J. Organomet. Chem. 2006, 691, 413-421.

80. "Recent Advances in Metalla-aromatic Chemistry." C. W. Landorf and M. M. Haley, Angew. Chem. Int. Ed. 2006, 45, 3914-3936 (invited review).

81. Carbon-Rich Compounds: From Molecules to Materials, M. M. Haley and R. R. Tykwinski, Eds., Wiley-VCH: Weinheim, 2006.

82. "Pioneers of Carbon-Rich Compounds." C. A. Johnson II and M. M. Haley, in Carbon-Rich Compounds: From Molecules to Materials, M. M. Haley and R. R. Tykwinski, Eds., Wiley-VCH: Weinheim, 2006, pp. 1-25.

83. "Biscyclization Reactions in Butadiyne- and Ethyne-linked Triazenes and Diazenes: Concerted vs. Stepwise Coarctate Cyclizations." L. D. Shirtcliff, A. G. Hayes, M. M. Haley, F. Köhler, K. Hess, and R. Herges, J. Am. Chem. Soc. 2006, 128, 9711-9721.

84. “The Phane Properties of [2.2]Paracyclophane/Dehydrobenzoannulene Hybrids.” H. Hinrichs, A. J. Boydston, P. G. Jones, K. Hess, R. Herges, M. M. Haley, and H. Hopf, Chem. Eur. J. 2006, 12, 7103-7115.

85. “The Renaissance of Annulene Chemistry.” E. L. Spitler, C. A. Johnson II, and M. M. Haley, Chem. Rev.2006, 106, 5344-5386 (invited review).

86. "Synthesis of 2H-Indazoles via Lewis-Acid Promoted Cyclization of 2-(Phenylazo)benzonitriles." L. D. Shirtcliff, J. Rivers, and M. M. Haley, J. Org. Chem. 2006, 71, 6619-6622.

87. "Two-Photon Absorption in 2-D Conjugated Quadrupolar Chromophores." A. Slepkov, F. A. Hegmann, R. R. Tykwinski, K. Kamada, K. Ohta, J. A. Marsden, E. L. Spitler, J. J. Miller, and M. M. Haley, Opt. Lett. 2006, 31, 3315-3317.

88. "Building Two-Dimensional, Symmetric Two-Photon Molecular Materials." A. Bhaskar, R. Guda, M. M. Haley, and T. Goodson III, J. Am. Chem. Soc. 2006, 128, 13972-13973.

89. "Systematic Structure-Property Investigations and Ion Binding Studies of Donor/Acceptor-Functionalized Tetrakis(arylethynyl)benzenes." E. L. Spitler, L. D. Shirtcliff, and M. M. Haley, J. Org. Chem. 2007, 72, 86-96.

90. "Cu- and Rh-Induced Migrations of Isoindazolyl Carbene/Carbenoids." L. D. Shirtcliff, R. Herges, and M. M. Haley, J. Org. Chem. 2007, 72, 2411-2418.

91. "Donor-Acceptor Substituted Tetrakis(phenylethynyl)benzenes as Emissive Molecules during Pulse Radiolysis in Benzene." S. Samori, S. Tojo, M. Fujitsuka, E. L. Spitler, M. M. Haley, and T. Majima, J. Org. Chem. 2007, 72, 2785-2793.

92. "Metallabenzenes and Valence Isomers. 9. Rearrangement of Iridabenzvalenes to Iridabenzenes and/or eta5-Cyclopentadienyliridium(I) Complexes: Experimental and Computational Analysis of the Influence of Silyl Ring Substituents and Phosphine Ligands." H.-P. Wu, D. H. Ess, S. Lanza, T. J. R. Weakley, K. N. Houk, K. K. Baldridge, and M. M. Haley, Organometallics 2007, 26, 3957-3968.

93. "Templated Synthesis of Pyridine-Functionalized Mesoporous Carbons through the Cyclotrimerization of Diethynylpyridines." Y. Shin, G. E. Fryxell. C. A. Johnson II, and M. M. Haley, Chem. Mater. 2008, 20, 981-986.

94. "Dynamic Proton-Induced Two-Stage Emission Switching in Donor-Functionalized Dehydrobenzopyrid[15]annulenes." E. L. Spitler, S. P. McClintock, and M. M. Haley, J. Org. Chem. 2007, 72, 6692-6699.

95. "Reactions in the Conjugated 'Ene-Ene-Yne' Manifold: Five-Membered Ring Fragmentation and Ring Formation via Coarctate/Pseudocoarctate Mechanisms." L. D. Shirtcliff, S. P. McClintock, and M. M. Haley, Chem. Soc. Rev. 2008, 37, 343-364.

96. "Synthesis of Dehydrobenzo[18]annulene Derivatives and Formation of Self-Assembled Monolayers: Implication of Core Size on Alkyl Chain Interdigitation." K. Tahara, C. A. Johnson II, T. Fujita, M. Sonoda, F. De Schryver, S. De Feyter, M. M. Haley, and Y. Tobe, Langmuir 2007, 23, 10190-10197.

97. "Carbon Networks Based on Benzocyclynes. 6. Synthesis of Graphyne Substructures via Directed Alkyne Metathesis." C. A. Johnson II, Y. Lu, and M. M. Haley, Org. Lett. 2007, 9, 3725-3728.

98. "Synthesis and Properties of Annulenic Subunits of Graphyne and Graphdiyne Nanoarchitectures." M.M. Haley, Pure Appl. Chem. 2008, 80, 521-534.

99. "Water and Hydrogen Halides Serve the Same Structural Role in a Series of 2+2 Hydrogen Bonded Dimers: 2,6-Bis(2-anilinoethynyl)pyridine Sulfonamides as Molecule and Ion Receptors." O. B. Berryman, C. A. Johnson II, L. N. Zakharov, M. M. Haley, and D. W. Johnson, Angew. Chem. Int. Ed. 2008, 47,117-120.

100. "Structure-Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes." E. L. Spitler, J. M. Monson, and M. M. Haley, J. Org. Chem. 2008, 73, 2211-2223.

101. “Synthesis of 1-Substituted Benzo[c]isoxazol-3(1H)-imines via Tandem Nitroso-Ene/Intramolecular Cyclizations of 2-Nitrosobenzonitrile.” J. L. Jeffrey, S. P. McClintock, and M. M. Haley, J. Org. Chem. 2008, 73, 3288-3291.

102. “Synthesis and Structure-Property Relationships of Donor/Acceptor-Functionalized Bis(dehydrobenzo[18]annuleno)benzenes.” E. L. Spitler and M. M. Haley, Org. Biomol. Chem. 2008, 6, 1569-1576.

103. “Fine-Tuning of Radiolysis Induced Emission by Variable Substitution of Donor/Acceptor-Substituted Tetrakis(arylethynyl)benzenes.” S. Samori, S. Tojo, M. Fujitsuka, E. L. Spitler, M. M. Haley, and T. Majima, J. Org. Chem. 2008, 73, 3551-3558.

104. “Structure-Property Investigations of Conjugated Thiophenes Fused onto a Dehydro[14]annulene Scaffold.” M. J. O'Connor, R. B. Yelle, L. N. Zakharov, and M. M. Haley, J. Org. Chem. 2008, 73, 4424-4432.

105. “Dynamic Proton-Induced Two-Stage Emission Switching in Donor-Functionalized Bis(dehydrobenzo[n]annuleno)benzenes and 1,2,4,5-Tetrakis(phenylethynyl)benzene.” E. L. Spitler and M. M. Haley, Tetrahedron 2008, 64, 11469-11474 (Symposium-in-Print).

106. “Computational Analysis of the Dual Reactivity of Conjugated ‘Ene-Ene-Yne’ Systems.” S. P. McClintock, L. D. Shirtcliff, M. M. Haley, and R. Herges, J. Org. Chem. 2008, 10, 3973-3976.

107. “Synthesis and Properties of Butyl-Capped Dehydrothieno[14]annulenes and their Conversion into Co-Planarized Terthiophenes.” M. J. O'Connor and M. M. Haley, Org. Lett. 2008, 73, 8755-8762.

108. “Synthesis and Properties of Conjugated Thiophenes Fused onto a Dehydro[15]annulene Scaffold.” M. J. O'Connor, R. B. Yelle, T. S. Linz, and M. M. Haley, Comptes Rendus Chimie 2009, 12, 385-394.

109. "Taming the Highly Reactive Oxonium Ion." M. M. Haley, Angew. Chem. Int. Ed. 2009, 48, 1544-1545

110. "Protonation Activates Anion Binding and Alters Binding Selectivity in New Inherently Fluorescent 2,6-Bis(2-anilinoethynyl)pyridine Bisureas." C. N. Carroll, O. B. Berryman, C. A. Johnson II, L. N. Zakharov, M. M. Haley, and D. W. Johnson, Chem. Commun. 2009, 2520-2522.

111. "Emission from Regioisomeric Bis(phenylethynyl)benzenes during Pulse Radiolysis." S. Samori, S. Tojo, M. Fujitsuka, T. Ryhding, A. G. Fix, B. M. Armstrong, M. M. Haley, and T. Majima, J. Org. Chem. 2009, 74, 3776-3782.

112. "Synthesis of a-Ketoester- and a-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems." S. P. McClintock, N. Forster, R. Herges, and M. M. Haley, J. Org. Chem. 2009, 74.

113. "Metallabenzenes and Valence Isomers. 10. Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-Aromatics." V. Jacob, C. W. Landorf, L. N. Zakharov, T. J. R. Weakley, and M. M. Haley, Organometallics 2009, 28.

114. "Anion Binding Induces Helicity in a Hydrogen Bonding Receptor: Crystal Structure of a 2,6-Bis(anilinoethynyl)pyridinium Chloride." C. A. Johnson II, O. B. Berryman, A. C. Sather, L. N. Zakharov, M. M. Haley, and D. W. Johnson, Cryst. Growth Des. 2009, 9.

115. “Spatial Control of Entangled Two-Photon Absorption with Organic Chromophores.” A. Guzman, M. Harpham, Ö. Süzer, M. M. Haley, and T. Goodson III, J. Am. Chem. Soc. 2010, 132,7840-7841.

116.“Self-Assembled Monolayers of Alkoxy-Substituted Octadehydrodibenzo[12]annulenes on Graphite Surfaces: A Design Strategy for peri-Benzopolyacene Formation.” K. Tahara, K. Inukai, N. Hara, C. A. Johnson II, M. M. Haley, Y. Tobe, Chem. Eur. J. 2010, 16, 8319-8328.

117. “Arylethynyl Receptors for Anions and Emerging Applications in Cellular Imaging.” C. N. Carroll, J. J. Naleway, M. M. Haley and D. W. Johnson, Chem. Soc. Rev. 2010, 39, 3875-3888 (invited review).

118. “Synthesis and Photophysical Properties of Expanded Dehydrobenzoannulenoannulene Trefoils.” T. Takeda, A. G. Fix, and M. M. Haley, Org. Lett. 2010, 12, 3824-3827.

119.“On the Road to Carbyne.” M. M. Haley, Nature Chem. 2010, 2, 912-913.

120. “Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes.” D. T. Chase, B. D. Rose, S. P. McClintock, L. N. Zakharov, and M. M. Haley, Angew. Chem. Int. Ed. 2011, 50, 1127-1130.

121. “Two-photon Absorption Properties of Two-Dimensional π-Conjugated Chromophores: Combined Experimental and Theoretical Study.” K. Ohta, S. Yamada, K. Kamada, A. D. Slepkov, F. A. Hegmann, R. R. Tykwinski, L. D. Shirtcliff, M. M. Haley, P. Sałek, F. Gel’mukhanov, and H. Ågren, J. Phys. Chem. A 2011, 115, 105-117.

122. “Coarctate versus Pericyclic Reactivity in Naphthalene-Fused Azo-Ene-Ynes: Synthesis of Benzocinnolines and Benzoisoindazoles.” S. P. McClintock, L. N. Zakharov, R. Herges, and M. M. Haley, Chem. Eur. J. 2011, 17, 6798-6806.

123. “Anion-Dependent Fluorescence in Bis(anilinoethynyl)pyridine Derivatives: Switchable ON-OFF and OFF-ON Responses.” C. N. Carroll, B. A. Coombs, S. P. McClintock, C. A. Johnson II, O. B. Berryman, D. W. Johnson, and M. M. Haley, Chem. Commun. 2011, 47, 5539-5541.

124. “Synthesis, Crystal Structures, and Photophysical Properties of Electron-Accepting Diethynylindeno-fluorenediones.” B. D. Rose, D. T. Chase, C. D. Weber, L. N. Zakharov, M. C. Lonergan, and M. M. Haley, Org. Lett. 2011, 13, 2106-2109.

125. “Incorporating BODIPY Fluorophores into Tetrakis(arylethynyl)benzenes.” D. T. Chase, B. S. Young, and M. M. Haley, J. Org. Chem. 2011, 76, 4043-4051.

126. “Lithium Cation Enhances Anion Binding over Sodium Cation in a Phosphine Oxide Based Tripodal Ditopic Receptor.” J. V. Gavette, J. Lara, O. B. Berryman, L. N. Zakharov, M. M. Haley, D. W. Johnson, Chem. Commun. 2011, 47, 7653-7655.

127. “Electron-Accepting 6,12-Diethynylindeno[1,2-b]fluorenes: Synthesis, Crystal Structures, & Photophysical Properties.” D. T. Chase, A. G. Fix, B. D. Rose, C. D. Weber, S. Nobusue, C. E. Stockwell, L. N. Zakharov, M. C. Lonergan and M. M. Haley, Angew. Chem. Int. Ed. 2011, 50, 11103-11106.

128. “Phenanthrene-Fused Azo-Ene-Ynes: Synthesis of Dibenzo[f,h]cinnoline and Dibenzo[e,g]isoindazole Derivatives.” B. S. Young, F. Koehler, R. Herges and M. M. Haley, J. Org. Chem. 2011, 76, 8483-8487.

129. “Molecular Self Assembly: Solvent Guests Tune the Conformation of a Series of 2,6-Bis(2-anilino-ethynyl)pyridine Based Ureas.” J. M. Engle, P. S. Lakshminarayanan, C. N. Carroll, L. N. Zakharov, M. M. Haley and D. W. Johnson, Cryst. Growth Des. 2011, 11, 5144-5152.

130. “Synthesis and Optoelectronic Properties of 2,6-Bis(2-anilinoethynyl)pyridine Scaffolds.” J. M. Engle, C. N. Carroll, D. W. Johnson and M. M. Haley, Chem. Sci. 2012, 3, 1105-1110.

131. “Diazaheterocyclic Analogues of Tetracene: Synthesis and Properties of a Naphtho-Fused Cinnoline and a Naphtho-Fused Isoindazole.” B. S. Young, J. L. Marshall, E. MacDonald, C. L. Vonnegut and M. M. Haley, Chem. Commun. 2012, 48, 5166-5168.

132. “Fluoreno[4,3-c]fluorene: A Closed-Shell, Fully-Conjugated Hydrocarbon.” B. D. Rose, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Org. Lett. 2012, 14, 2426-2429.

133. “6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics and Ambipolar OFETs.” D. T. Chase, A. G. Fix, S. J. Kang, B. D. Rose, C. D. Weber, Y. Zhong, L. N. Zakharov, M. C. Lonergan, C. Nuckolls and M. M. Haley, J. Am. Chem. Soc. 2012, 134, 10349-10352.

134. “Dimerization Reaction of Regioisomeric Bis(phenylethynyl)benzene Radical Anions during Pulse Radiolysis.” M. Fujitsuka, S. Samori, S. Tojo, M. M. Haley and T. Majima, ChemPlusChem 2012, 77, 682-687.

135. “Coarctate Cyclization Reactions: A Primer.” B. S. Young, R. Herges and M. M. Haley, Chem. Commun. 2012, 48, 9441-9455 (invited Feature Article).

136. “Formation of the Donor-Acceptor Charge Transfer Exciton and its Contribution to Charge Photogeneration and Recombination in Small-Molecule Bulk Heterojunctions.” M. J. Kendrick, A. Neunzert, M. M. Payne, B. Purushothaman, B. D. Rose, J. E. Anthony, M. M. Haley and O. Ostroverkhova, J. Phys. Chem. C 2012, 116, 18108-18116.

137. “Indenofluorenes and Derivatives: Syntheses and Emerging Materials Applications.” A. G. Fix, D. T. Chase and M. M. Haley, in Topics in Current Chemistry, Volume 356, J. S. Siegel and Y.-T. Wu, Eds., Springer: Berlin, 2012, in press (invited review).

138. “Doubly Coarctate-Stabilized Carbenes: Synthetic and Computational Studies” B. S. Young, R. Herges and M. M. Haley, J. Org. Chem. 2012, 77, Accepted.

138. “Lithium-Selective Phosphine Oxide-Based Ditopic Receptors Show Enhanced Halide Binding Upon Alkali Metal Ion Coordination.” J. V. Gavette, J. Lara, L. L. Reling, M. M. Haley and D. W. Johnson, Chem. Sci. 2012, 3, accepted.