Self-Sorting of Dynamic Combinatorial Libraries

Nature is a master of chemoselectivity: in a typical biological cell, hundreds of reactions occur simultaneously, but without any interference, in a complex "soup" of biological precursors. We are seeking to replicate this behavior in complex libraries of synthetic compounds known as dynamic combinatorial libraries (DCLs). We have shown that libraries of as many as 100 members can be reduced in complexity to just a handful of discrete compounds, produced in high purities.

Reviewed in Chem 2017, 2, 502–524

Porous Materials and Porous Molecular Crystals

Porous materials have a plethora of application in industry, mostly related to energy technologies. We are particularly interested in the synthesis of metal-organic and fully organic porous frameworks through the use of sophisticated organic precursors that assemble into porous structures either on their own, or upon coordination to metals. These frameworks have found applications in binding of fluorocarbons, Freons (CFCs) and fluorinated anesthetics.

Reviewed in Org. Mater. 2019, 1, 19–29

Cyclobenzoins

In 2015, we have discovered that benzoin condensation of small aromatic dialdehydes leads to the generation of cyclic trimeric and tetrameric adducts, which we dubbed cyclobenzoins. These new macrocycles are characterized by exceedingly simply synthesis, rigid cavities, and rich chemistry that harks back to the early 19th century days of benzoin condensation.

Reviewed in Chem. Commun. 2018, 54, 11989–11997

Rigid Aromatic Fluorophores

We have developed cross-conjugated X-shaped fluorophores based on benzobisoxazole and benzimidazole nuclei. In these molecules, appropriate substitution of the x- and y-axes results in the spatial isolation of FMOs, leading to predictable and useful sensing response. These systems have been utilized as sensors for carboxylic and boronic acids, phenols, amines, and various anions. More recently, our interest have expandedto the aggregation-induced emission in precursors to porous molecular crystals.

Reviewed in Acc. Chem. Res. 2014, 47, 2074–2083

The Miljanić lab relies on supramolecular and synthetic chemistry as its key tools. Synthesis is used in the broad sense of the word, encompassing organic, coordinative inorganic, and organometallic preparations. Spectroscopy, crystallography, and materials characterization are the most relevant analytical tools. Students and postdoctoral researchers in the Miljanić group receive detailed guidance in scientific writing and visualization. This diversified training is intended to prepare them for challenges in both academic and a variety of industrial work environments.