This EAGER project is aimed at investigating the edge- on chemical gating effect on electronic properties of semiconducting molecules and materials. Three molecules resembling a field effect transistor and containing a three-dimensional rigid cyclophane structure were synthesized. Theoretical calculations indicated dramatic changes in molecular orbital distribution as a function of the nature of substituents, indicating the potential to observe edge-on gating effect. A break-junction STM system was set-up recently for measuring charge transport through single molecule. A preliminary result is shown here. Furthermore, several polymers containing cyclophane were synthesized, which undergo self-assemble in the presence of halogen-bonding partner into porous material structures. It is clear now that this EAGER project is finding firm footing for expanding into a full scale research effort. Cyclophane incorporated into polymer and single molecule systems for applications in organic electronics Calculations showing the HOMO and LUMO of the cyclophane transistor molecule STM system modified for break junction technique SEM images of porous structures in cyclophane polymer Conductance curve of molecular transistor EAGER: Chemical Design for Controlling Electronic Properties of Organic Semiconductors and Molecules via Edge-On Gating Luping Yu, University of Chicago, DMR

Educational outreach and diversity: The Yu group have participated in the Leadership Alliance by offering summer research opportunities in the lab to those from under-represented minority groups. We have succeeded in recruiting a minority undergraduate student (Kevin Trujillo) from Loyola University Chicago to join us for the summer research. We will design a small but feasible synthetic project for students to undertake and gain experience. For example, we will start the training for these students in synthesizing the building motif, which is the nucleus for further synthetic effort. Industrial outreach: The Yu group collaborations with various industrial companies have generated very positive results, not only in financial arrangements for the PI’s research, but also intellectual progress. For example, several papers coauthored with Solarmer scientists have become listed among the most cited papers in the year Meanwhile, these collaborations can also lead to employment opportunities for students and postdoctoral associates. Last year, PI’s group has one student and a postdoctoral associate hired by Intel Corp. This proposed project offers a platform to continue these excellent efforts. We collaborated with IBM scientist in molecular electronics and published a paper recently. Arrangement has been made through our MRSEC for further collaboration with IBM on undergraduate student research. The Yu group participates in the industrial associates meeting: industrial opportunities for PhD students EAGER: Chemical Design for Controlling Electronic Properties of Organic Semiconductors and Molecules via Edge-On Gating Luping Yu, University of Chicago, DMR