Abstracts Book - IMRC 2018

• SF4-O005
SHINING LIGHT ON BORON-BASED SUPRAMOLECULAR
MATERIALS: A STRATEGY FOR THE SYNTHESIS OF ORGANIC
BUILDING BLOCKS
Gonzalo Campillo Alvarado 1 , Kyle Dmello 1 , Alexis D. Brannan 1 , Zhitting Feng 1 , Dale C.
Swenson 1 , S. V. Santhana Mariappan 1 , Hugo Morales Rojas 2 , Herbert Höpfl 2 , Leonard R.
Macgillivray 1
1 University of Iowa, Department of Chemistry, United States. 2 Universidad Autónoma del
Estado de Morelos, Centro de Investigaciones Químicas, Mexico.
Organoboron compounds are among the most versatile and valuable
intermediates in organic chemistry. Boronic acids, a class of organoboron
compounds, have also attracted attention in the field of supramolecular
chemistry owing to an ability to participate in multiple covalent and noncovalent
interactions.
Supramolecular interactions encompass a crucial role in the molecular packing
of crystals and solids as they constitute one end of the supramolecular
continuum and are formed by static self-assembly. In this context, boronic acids
and derivatives offer a broad window of opportunities to modulate and control
the properties and reactivity of solids.
In this presentation, I will discuss our efforts to develop strategies to direct [2 +
2]-photocycloadditions of pyridyl ethylenes in the solid state using boronic acids
and boronic esters. In the strategy, the components self-assemble by (B)O–
H···N hydrogen bonds and N–B dative bonds to generate UV-photoreactive
adducts. The resulting photoproducts show promising opportunities in the
context of host-guest chemistry as storage materials.
Acknowledgment:
We gratefully acknowledge financial support the National Science Foundation
(DMR-1408834), CONACYT-COVEICYDET and the University of Iowa Graduate
College for funding.
Keywords: [2 + 2]-photocycloadditions, supramolecular chemistry, boron-based
adducts
Presenting authors email: gonzalo-campillo-alvarado@uiowa.edu