Binding studies of tetrathiafulvalene-calix[4]pyrroles with electron-deficient guests

Tetrahedron

Volumn 64, Issue 36, 2008, Pages 8449-8463

  Nielsen, Kent A ^a   Martín Gomis, Luis ^b   Sarova, Ginka H ^c   Sanguinet, Lionel ^d   Gross, Dustin E ^e   Fernández Lázaro, Fernando ^b   Stein, Paul C ^a   Levillain, Eric ^d   Sessler, Jonathan L ^e   Guldi, Dirk M ^c   Sastre Santos, Ángela ^b   Jeppesen, Jan O ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^d UNIVERSITÉ D'ANGERS   (France)

^e UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Calix 4 pyrroles; Fullerenes; Molecular switches; Supramolecular chemistry; Tetrathiafulvalenes

Indexed keywords

2,5,7 TRINITRO 9 DICYANOMETHYLENEFLUORENE; AROMATIC NITRO COMPOUND; CALIX[4]PYRROLE; CALIXARENE; CHLORIDE ION; FLUORENE DERIVATIVE; FULLERENE DERIVATIVE; PYRROLE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; RECEPTOR BINDING; SUPRAMOLECULAR CHEMISTRY;

EID: 47949108710     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.141     Document Type: Article

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56. -1 has previously been reported for the complexation of 1 with chloride ions in 1,2-dichloroethane (DCE) at 298 K, see Refs. 11 and 13.
57. -.
58. Hexafluorophosphate was chosen as the counter anion, because all available evidence supports the notion that this anion has a very low affinity for receptor 1.
59. In principle, hydrogen bonding interactions can also take place between the NH protons of the receptor 1 and the carbonyl and ester groups present in guests 3 and 4.
60. See Supplementary data.
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63. A continuous variation UV-vis experiment was carried out to determine the stoichiometry of the binding interaction between receptor 1 and the bifunctional substrate 7. The resulting Job plot exhibited a maximum at a mole fraction of approximately 0.28. This is interpreted in terms of a 1:2 binding stoichiometry (1:7), see Supplementary data.
64. - and the bifunctional substrate 7 in dichloromethane solution. The resulting Job plot exhibited a maximum at a molar fraction of approximately 0.37. This is interpreted in terms of a 2:1 binding ratio between 1·Cl- and 7; see Supplementary data.
65. Estimated errors <15%.