Rigid Molecular Tweezers: Preorganized Hosts for Electron Donor-Acceptor Complexation in Organic Solvents

Steven C. Zimmerman, Craig M. VanZyl, Gregory S. Hamilton

Research output: Contribution to journalArticlepeer-review

Abstract

Novel nonmacrocyclic receptor molecules 1 and 7 have been synthesized which are capable of acting as molecular tweezers. These molecules are 7-aryl-2,12-bis(9-acridinyl)dibenz[c,h]acridines, which when unsymmetrically substituted exhibit atropisomerism. In addition to being rigid and providing a ca. 7 Å interchromophore distance, the dibenz[c,h]acridine spacer is the first to enforce a syn cofacial orientation of the complexing chromophores. 1H NMR studies indicate that 1 and 7 have open clefts. These preorganized clefts form highly oriented inclusion complexes with 2,4,7-trinitrofluorenone (TNF) in CDCl3 as monitored by 1H NMR. The complexation has a strong electron donor-acceptor component. As such, the association constants for TNF are dependent on the π-basicity of the host and range from 149 M-1 for tert-butyl-substituted 7b to 697 M-1 for dimethylamino-substituted 7f (CDCl3). Monoacridines and a flexible diacridine, under identical conditions, bind TNF very weakly (Kassoc < 5 M-1).

Original languageEnglish (US)
Pages (from-to)1373-1381
Number of pages9
JournalJournal of the American Chemical Society
Volume111
Issue number4
DOIs
StatePublished - Feb 1989

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Rigid Molecular Tweezers: Preorganized Hosts for Electron Donor-Acceptor Complexation in Organic Solvents'. Together they form a unique fingerprint.

Cite this