# Presentation: 886237

## Template-Controlled Solid-State Organic Synthesis

**Leonard R. MacGillivray, University of Iowa,**** ****DMR 0133138**

_**Scientific Merit**_**:** The MacGillivray group is transferring concepts between organic solid-state chemistry and organic synthesis.  The group aims to show how the organic solid state can be used as a ‘synthetic playground’ similar to the liquid phase.  Benefits of using the solid state as a playground include making molecules completely inaccessible in solution and under solvent-free conditions.  To achieve this goal, the MacGillivray group in a CAREER award is using molecular templates to assemble olefins, *via* either hydrogen bonds or coordination bonds, for [2+2] photodimerizations.  The group has used the approach to construct complex molecules such as ladderanes.  The funded research has resulted in a 2007 Arthur C. Cope Scholar Award of the American Chemical Society.

**[5]-ladderane**

**Notes:**
Who: Professor Leonard R. MacGillivray
Where: Department of Chemistry, University of Iowa
What: Research laboratory is developing a general method to control chemical reactivity in the organic solid state.
So What?: The organic solid state is an untapped medium for systematically controlling chemical reactivity.  The solid state differs from the liquid phase (i.e. where chemists ‘normally’ conduct synthetic chemistry) in that the solid state offers a solvent-free environment and can provide access to molecules that cannot be obtained in the liquid phase.  Controlling reactivity in the solid state can also lead to the development of unique devices for applications in ultra-high density data storage.

## Template-Controlled Synthesis: Undergraduate

**Laboratory, Working Weekends, and MOSSCS**
**Leonard R. MacGillivray, University of Iowa, DMR 0133138**

_**Immediate Relevance, Education and Outreach**_**:** The MacGillivray group has developed a undergraduate laboratory that involves the template method (*J. Chem. Ed.* **2005**, *82*, 1679).  Approximately 450 undergraduates have been introduced to the fields of solid-state, supramolecular, and green chemistry through the method.  The CAREER Award has also allowed us to develop a ‘Working Weekend’ tutorial that teaches undergraduate students from regional colleges in Iowa, Illinois, Missouri, and Wisconsin how to develop and process single-crystal X-ray structure data.  The MacGillivray group has also hosted the Midwest Organic Solid State Chemistry Symposium (MOSSCS) twice (2002, 2006) at the University of Iowa.

- Figure 2. Snapshot from X-ray crystallography
- tutorial developed at the University of Iowa.

- Figure 1. Photoreactor assembly used in the undergraduate green chemistry experiment.

**Notes:**
Who: Professor Leonard R. MacGillivray
Where: Department of Chemistry, University of Iowa
What: Research laboratory is developing a general method to control chemical reactivity in the organic solid state.
So What?: Being an untapped medium, it is not surprising that undergraduate students remain largely unaware of the benefits of synthetic chemistry in the organic solid state.  The MacGillivray group aims to break down this barrier by targeting ways to incorporate organic solid-state synthesis into undergraduate curricula and settings.  In doing so, the MacGillivray group has developed an undergraduate organic laboratory based upon the funded methodology.  The group has also developed a weekend tutorial on X-ray crystallography and has twice hosted MOSSCS.