Utilization of K-region oxidation for the synthesis of functional materials

Pyrene with its long fluorescence lifetime, large Stokes shift and proclivity towards excimer formation has become the gold standard in the sensing of microenvironments using fluorescence spectroscopy. Derivatives of pyrene find applications in a broad range of fields. However, the design of more complex systems is hampered by the lack of selectivity one encounters when working with pyrene. Alkylation, halogenation and nitration produce practically inseparable isomers. Methods that desymmetrize pyrene are currently of high value. Known methods have recently been improved and applied to a number of systems within the Bodwell group. The optimization of a K-region oxidation reaction and utilization of desymmetrized pyrene in the synthesis of redox-active molecules and progress towards a 2,7-pyrenylene-ethynylene macrocycle is investigated in this thesis work. References [1] R. Rieger, K. Müllen, J. Phys. Org. Chem., 2010, 23, 315-325. [2] J. Andréasson, U. Pischel, Chem. Soc. Rev., 2015, 44, 1053-1069. [3] P. Conlon, C. J. Yang, Y. Wu, Y. Chen, K. Martinez, Y. Kim, N. Stevens, A. A. Marti, S. Jockusch, N. J. Turro, W. Tan, J. Am. Chem. Soc., 2008, 130, 336-342

Synthesis, structure and function of oligo(1,8-pyrenylenes)

This thesis is divided into four chapters. Chapter 1 will show progress towards a review of applications utilizing the pyrene core to show the utility of one of the most studied molecules in chemistry is far from fully realized. Chapter 2 shows a monomer‐through-pentamer series of oligo(1,8‐pyrenylene)s was synthesized using a two‐step iterative synthetic strategy. The trimer, tetramer and pentamer are mixtures of atropisomers that interconvert slowly at room temperature (VTNMR analysis). They are classified as functional molecular liquids (FMLs) well below room temperature, as indicated by POM, DSC and SWAXS analysis. The oligomers are highly fluorescent both in the liquid state and in dilute solution and an investigation of their photophysical properties demonstrated that delocalization plays a larger role in their excited states than it does in related pyrene‐based oligomers. Chapters 3 and 4 outline progress in using the oligomers as starting points for different molecular systems will also be covered, attempting to put more ‘F’ in the FMLs

Bending Pyrenacenes to Fill Gaps in Singlet-Fission-Based Solar Cells

Singlet fission is envisaged to enhance the efficiency of single-junction solar cells beyond the current theoretical limit. Even though sensitizers that undergo singlet fission efficiently are known, characteristics like low-energy triplet state or insufficient stability restrict their use in silicon-based solar cells. Pyrenacenes have the potential to overcome these limitations, but singlet-fission processes in these materials is outcompeted by excimer formation. In this work, bent pyrenacenes with a reduced propensity to stack and thus form excimers are computationally evaluated as singlet-fission materials. The energies of the S1, T1 and T2 states were estimated in a series of bent pyrenacenes by means of time-dependent density functional theory calculations. Our results show the opposite trend observed for perylene diimides, namely, an increase in the energy of the T1 and S1 states upon bending. In addition, we show that the energy levels can be tuned on demand by manipulating the bend angle to match the energy gap of various semiconductors that can be used in single-junction solar cells, making pyrenacenes promising candidates for singlet fission

The Grizzly, February 18, 2010

Every Ending Starts with a Beginning • Record-Breaking Blizzard Evokes Varied Reactions • Could Watching the Super Bowl Damage Your Heart? • Snow Storm Photos • Senior Class Gift Drive • SPINTfest \u2710 Brings New Themes for Houses • UC Goes Red to Raise Awareness About the Risks of Heart Disease • Opinion: Teenage Pregnancy TV Shows are a Big Hit, But What\u27s the Effect? • Tragedy Strikes in Early Hours of Winter Olympics • Men\u27s Basketball Shuts Down McDanielhttps://digitalcommons.ursinus.edu/grizzlynews/1806/thumbnail.jp

The Grizzly, April 14, 2011

Ursinus Enjoys Sixth Annual CoSA Event • Students Participate in 30 Hour Famine • Haverford Professor Guest Lectures on Physics Theory • Dr. Ruth Rosenberg Speaks on Holocaust Remembrance • Ursinus Welcomes Patti Smith • Tips on Surviving and Salvaging Bad Internships • Hypnotist Brings Laughs • How to Avoid Allergy Season • Linking Up with LinkedIn • Internship Spotlight: Lindsay Budnick • Opinions: Response to Article Segregation in the 21st Century ; Verizon\u27s DroidX-R2D2 has Cool Features But is Not for Me; President Obama Sends CIA Agents to Libya • How Far Ursinus Goes to Keep Students Safe on Main Street • New Coach and New Outlook Lead UC Softball • Gymnasts Named All-Americans at Championshipshttps://digitalcommons.ursinus.edu/grizzlynews/1834/thumbnail.jp

The Grizzly, February 12, 2010

Main Street Renovation Improves Safety • Community Brings Down Crime at Ursinus College • Annual Scottish Irish Festival This Weekend • Bonner Leaders Hold Fair in Lower Wismer • What You Should Really Expect from Study Abroad • New Member Education Starts Up Again and Looks Forward to Positive Change • UC Gymnastics is Flipping Through 2010 Season • Moliken Named New Athletic Directorhttps://digitalcommons.ursinus.edu/grizzlynews/1805/thumbnail.jp

The Grizzly, April 8, 2010

First Annual Backwards Beauty Pageant Held • Ursinus Senior to Travel Abroad for a Year with Watson • Kappa Alpha Psi and Seismic Step Emerge on Campus • UC Welcomes New Field Hockey Coach • Sex on Wheels Documentary Screening • Volunteering with St. Christopher\u27s Children\u27s Hospital • Feeling Good in The Skin We\u27re In • The Sacrifice Your Body Makes for [Better] Grades • Opinion: Kyleigh\u27s Law Profiles Drivers by Age in New Jersey • Upper Classmen Off-Campus Living • UC Gymnastics Closes Season with Successhttps://digitalcommons.ursinus.edu/grizzlynews/1810/thumbnail.jp

The Grizzly, September 16, 2010

Activities Fair Brings Light to Organizations • Computer Science Students Begin Exciting New Projects • UC United Society of Leaders Emerges on Campus • Brandon Kamin Launches into MC Role for ABC\u27s Show Eaglemania • Calorie Counting Hits Zack\u27s • Theater Preview • Meet up with Two New Professors on Campus • Blend Cafe Hosts Open Mic Night for Students and Community • Opinions: Primaries are More Overrated Than They are Important; Unpredictable Turmoils of the Unreliable Ursinus WiFi • Ursinus Women\u27s Volleyball Heads Into Promising Seasonhttps://digitalcommons.ursinus.edu/grizzlynews/1817/thumbnail.jp

The Grizzly, February 10, 2011

Bonners Give Insight on Organization • Kappa Alpha Psi Fraternity to Participate in Spring Intake • Future UC President Dr. Bobby Fong Receives National Award • Ursinus College Plays Host to W. R. Crigler • GRE Makeover and Helpful Hints to Ace the Test • Calvin Levels Performs One Man Show in the Blackbox • New Program Brings Students and Professors Closer • Internship Profile: Matt Angle • Opinion: UC Town Hall Meeting Proved a Bit Disappointing; Letter to a Writer; A Multicultural Ursinus Campus on the Way; Upheaval in the Middle East: Why Students Should Care • Murren Adds Name to History Books During Seasonhttps://digitalcommons.ursinus.edu/grizzlynews/1829/thumbnail.jp

The Grizzly, October 28, 2010

Junot Diaz Speaks to Ursinus Campus • Berman Celebrates 20th Anniversary with Open House • Active Minds Talks About Mental Illness • Ursinus Music Department Active on Campus • UC Homecoming 2010 • Senior Explores Middle East • Students Celebrate Writing • Internship Spotlight: Jason Ward • Finally, Ursinus Creates an Arena for Race Relations • Once Upon a Potty • Letter to the Editor • Hey UC, Give Me a [Fall] Break • Bears Travel in Packs During Cross Country Season • Women\u27s Rugby Takes on Scranton This Saturdayhttps://digitalcommons.ursinus.edu/grizzlynews/1822/thumbnail.jp