Modulation of N?I and ~+N-H?Cl~-?I halogen bonding: Folding, inclusion, and self-assembly of tri-and tetraamino piperazine cyclophanes

Raatikainen K.; Rissanen K.

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Modulation of N?I and ~+N-H?Cl~-?I halogen bonding: Folding, inclusion, and self-assembly of tri-and tetraamino piperazine cyclophanes

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The acidity of the crystallization conditions was successfully employed in modulating the balance between the robust intramolecular hydrogen bonding (HB) and intermolecular halogen bonding (XB) observed in large tri-(1) and tetraamino (2) piperazine cyclophanes. A careful crystallization of the title XB acceptor cyclophanes with a strong bidentate XB donor 1,4-diiodotetrafluorobenzene (F4DIB) from CHCl_3:MeOH, dimethylformamide (DMF), or HCl:H _2O:EtOH resulted in X-ray quality crystals of 1·F4DIB, 2@DMF, 2·2@F4DIB, 1H_3Cl_3·(F4DIB)_6, and 2H_6Cl_6·(F4DIB)_2. The intramolecular hydrogen bonding pattern in 1 and 2 was retained in neutral protic and aprotic solvents, and regular N-H?N hydrogen and C-I?N halogen bonding synthons were observed for 1·F4DIB, 2@DMF, and 2·2@F4DIB. Because of its unaffected Pac-Man (alias Pacman) motif, cyclophane 2 manifested a size-selective complexation of DMF over F4DIB under neutral conditions. Acidic conditions led to the protonation of the cyclophanes, and ~+N- H?Cl~-, C_(PFC)-I?Cl~-, and C _(PFC)-I?Cl~-?I-C_(PFC) synthons appeared as structural elements. The C_(PFC)-I?Cl ~-?I-C_(PFC) anion resulted in the first XB rotaxane motif which was observed in 1H_3Cl_3·(F4DIB) _6 where the chloride anion was bound in the center of 1 via EtOH-mediated hydrogen bonding.

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《Crystal growth & design》 |2010年第8期|3638-3646|共9页
作者
Raatikainen K.; Rissanen K.;
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Department of Chemistry, Nanoscience Center, University of Jyv?skyl?, P.O. Box 35, FIN-40014, Finland;

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正文语种英语
中图分类晶体学;
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Modulation of N?I and ~+N-H?Cl~-?I halogen bonding: Folding, inclusion, and self-assembly of tri-and tetraamino piperazine cyclophanes

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