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Organic Spectroscopy


Determination of Absolute Stereochemistry Using Exciton Coupled Circular Dichroism (ECCD)



Our venture in the field of asymmetric reactions have motivated us towards a simplistic approach in building small chiral motifs that can potentially trigger a variety of useful transformations with a high level of enantiocontrol. In the area of Organic Spectroscopy, we are interested in developing host/guest systems that can be used in the absolute stereochemical determination of chiral compounds. We accomplish this through the design and synthesis of chromophoric receptors, which upon binding with the chiral compound function as reporters of chirality. We rely heavily on Circular Dichroism (CD) as the tool for observing the host/guest interactions between the chiral compounds and the receptors. In particular, we will take advantage of the excitonic coupling between independently conjugated chromophores that make up the receptors to establish non-empirical guidelines for the absolute stereochemical determination of asymmetric centers.






Recent Publications


  1. Gholami, H.; Anyika, M.; Zhang, J.; Vasileiou, C.; Borhan, B. "Host-Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry", Chem.Eur.J. 2016, 22(27), 9235-9239. [PDF]
  2. Tanasova, M.; Anyika, M.; Borhan, B. "Sensing Remote Chirality: Stereochemical Determination of beta-, gamma-, and delta-Chiral Carboxylic Acids", Angew. Chem. Int. Ed. Engl. 2015, 54, 4274-4278. [PDF]
  3. Anyika, M.; Gholami, H.; Ashtekar, K. D.; Acho, R.; Borhan, B. "Point-to-Axial Chirality Transfer—A New Probe for "Sensing" the Absolute Configurations of Monoamines", J. Am. Chem. Soc. 2014, 136, 550-553. [PDF]
  4. Li, X.; Burrell, C.; Staples, R. J.; Borhan, B. "Absolute Configuration of 1,n-Glycols: A Nonempirical Approach to Long-Range Stereochemical Determination", J. Am. Chem. Soc. 2012, 134, 9026-9029. [PDF]
  5. Tanasova, M.; Borhan, B. "Conformational Preference in Bis(porphyrin) Tweezer Complexes: A Versatile Chirality Sensor for -Chiral Carboxylic Acids", Eur. J. Org. Chem. 2012, 12, 3261-3269. [PDF]