Calixarenes and their Applications from the perspective of their creator, Carl David Gutsche

1. C. David Gutsche
Macromolecular People
Aman Imani
Macalester College, MN

2. The Beginning
- Born March 21, 1921 in Oak Park, IL
- Family: wife, 3 kids and grandchildren
Education
- B.A. Oberlin College (1943-1947)
- Ph.D. University of Wisconsin (1947-1951) under William Summer Johnson
- WARF Post-doctoral fellow at U. Wisconsin

3. Professional Life
- (1970-1976): Washington (St. Louis) Chem Dept. Chair
- (1947-1989): Spent 42 years at Washington (St. Louis)
- (1989-2002): Texas Christian University (13 years)
- 165 journal articles;
- 6 books (including major textbook [1975] in Organic Chemistry)
- Numerous chapters in books

4. Research interests
- Organic chemistry (Diazoalkane-Carbonyl Reactions, Carbene Chemistry,
Photochemistry, Boroxazolidines, Polylfunctional Catalysis, Enzyme Mimics,
Micellar Catalysis);
- Calixarenes (for which he is most noted); pioneered field of calixarene
chemistry

5. Cyclodextrins
● Produced by Starch
● Can form host-guest complexes, act as
strong catalysts
● Problem: Only come in a small number of
sizes

6. Calixarenes
- Calixarenes??
- Nomenclature
- All same abilities as
Cyclodextrins and
more
- Many ring variations

7. Synthesis
- Aromatic components from phenol, resorcinol or pyrogallol.
- Aldehyde (formaldehyde, acetaldehyde, etc.)
- Electrophilic Aromatic Substitution (EAS)
- Elimination of water
- Second aromatic substitution
- Acid catalysed or base catalysed

8. EAS
water
2nd
EAS

9. Biological applications
- Carriers through membranes (amphiphilic)
- Amino acid targets & immobilization proteins
- DNA chips (HPV detection)
- Cancer and tumor prevention
- Genome editing
- In vivo & in vitro experiments

10. Applications (contd..)
- Host-Guest Complexes: E.g. Metal Ion Transport Agents
- Enzyme mimics (ability to attach various functional groups)
- Catalyst
- Purification/ Filtration of chemicals
- Nanocapsules
- Sensors

11. Bibliography
● Gutsche, C. David. "Calixarenes." Accounts of Chemical Research 16.5 (1983): 161-170.
● Jr., Julius Rebek. "Host–guest Chemistry of Calixarene Capsules." Chemical Communications 8 (2000): 637-43. Web.
● Perrin, R., R. Lamartine, and M. Perrin. "The Potential Industrial Applications of Calixarenes." Pure and Applied Chemistry 65.7
(1993): 1549-559. Web.
● Mchahon, Gillian, Shane O'malley, and Kieran Nolan. "Important Calixarene Derivatives : Their Synthesis and Applications."
ChemInform 35.23 (2004): n. pag. Web.
● Nimse, Satish Balasaheb, and Taisun Kim. "Biological Applications of Functionalized Calixarenes." Chemical Society Reviews 42.1
(2012): 366. Web.
● Mcmahon, Gillian. "Important Calixarene Derivatives – Their Synthesis and Applications." Arkivoc 2003.7 (2002): 23. Web.