基于二氮中环化合物和有机酸的二元离子型氢键超分子体系构筑
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摘要
利用结构相似的有机碱1，4-二氮环己烷(PIPO)和1，4-二氮环庚烷(DACH)在室温下有选择性地与有机羧酸(包括刚性芳香酸及柔性脂肪酸)反应制备了一系列质子转移的有机二元共晶，这些晶体包括第二章中的[H_2DACH]·[OA](1a)，[H_2PIPO]·[OA]·H_2O(1b)，[H_2DACH]·[FA](2a)，[H_2PIPO]·[FA](2b)，[H_2DACH]·[TA](3a)，[H_2PIPO]·[TA](3b)，[H_2DACH]·[PNA]_2(4a)，[H_2PIPO]·[PNA]_2(4b)，[H_2DACH]·[NDA]·3H_2O(5a-1)，[H_2DACH]·[HNDA]_2·(H_2O)·(CH_3OH)(5a-2)，[H_2PIPO]·[NDA]·H_2O(5b)，[H_2DACH]·[HTMA]·H_2O(6a)，[H_2PIPO]·[H_2TMA]_2(6b)，[H_2DACH]_2·[BTA]·2.5H_2O(7a-1)，[H_2DACH]_2·[BTA]·4.5H_2O(7a-2)，and[H_2PIPO]_2·[BTA]·6.5H_2O(7b)和第三章中的[(H_2PIPO)·(HBTC)](17)，[(H_2PIPO)·(HA)](18)，[(H_2PIPO)·(HCA)·H_2O](19)，[(H_2PIPO)·(PA)·3H_2O](20)。
X-射线单晶衍射结果表明，在所有这些二元共晶结构中，有机酸和有机碱之间发生质子转移，导致形成强N-H…O氢键相互作用，并在此基础上揭示了这些氢键相互作用在形成空间网络结构中的导向功能。因此，在这些晶体中，由若干不同氢键形成了1D链以及2D和3D网络结构。热重(TGA)结果表明其热稳定性与晶体氢键的强度以及强氢键的数目密切相关。并进一步探讨了此类柔性羧酸和刚性羧酸与PIPO和DACH所形成的各种超分子结构的异同，丰富了相关晶体工程的研究。
Analogous diazamesocycles 1,4-diazacycloheptane (DACH) and piperazine (PIPO) bases were rationally chosen to crystallize with a range of organic acids (including aromatic and alkyl carboxylic acids), affording two series of binary charge-assistant co-crystals, which are characterized and structurally dicussed in this work.
In chapterⅡ, sixteen diamine carboxylate are synthesized through self-assembly of DACH or PIPO with multiple carboxylic acids. The resultant compounds are as follows: [H_2DACH]·[OA](1a), [H_2PIPO]·[OA]·H_2O(1b), [H_2DACH]·[FA] (2a), [H_2PIPO]·[FA] (2b), [H_2DACH]·[TA] (3a), [H_2PIPO]·[TA](3b), [H_2DACH]·[PNA]_2 (4a), [H_2PIPO]·[PNA]_2(4b), [H_2DACH]·[NDA]·3H_2O(5a-1), [H_2DACH]·[HNDA]_2·(H_2O)·(CH_3OH) (5a-2), [H_2PIPO]·[NDA]·H_2O (5b), [H_2DACH]·[HTMA]·H_2O(6a), [H_2PIPO]·[H_2TMA]_2(6b), [H_2DACH]_2·[BTA]·2.5H_2O (7a-1), [H_2DACH]_2·[BTA]·4.5H_2O (7a-2), and [H_2PIPO]_2·[BTA]·6.5H_2O (7b). All the prepared co-crystals have a common feature of the occurrence of the proton-transfer between acid and base. Strong N-H...O interactions are involved in these co-crystals, undoubtedly following the best donor/acceptor guidelines.
And in chapterⅢ, four PIPO related compounds are obtained under general conditions. they are [(H_2PIPO)·(HBTC)] (17), [(H_2PIPO)·(HA)] (18), [(H_2PIPO)·(HCA)·H_2O] (19), [(H_2PIPO)·(PA)·3H_2O] (20). Proton-transfer has also been detected in these compounds.
X-ray single-crystal diffraction studies reveal that the stronger N-H...O and O-H...O interactions, are the driving forces for the construction of the hydrogen-bonding networks in these compounds. Thus, 1D chain structure, 2D framework and 3D framework are constructed in these compounds by multiple hydrogen bonds. Thermogravimetric analysis (TGA) of mass loss for twenty compounds has been measured in this work. The similarity in motifs of aromatic or alkyl dicarboxylic acid with DACH and PIPO functional groups is extended to synthons for prospering crystal engineering.
X-射线单晶衍射结果表明，在所有这些二元共晶结构中，有机酸和有机碱之间发生质子转移，导致形成强N-H…O氢键相互作用，并在此基础上揭示了这些氢键相互作用在形成空间网络结构中的导向功能。因此，在这些晶体中，由若干不同氢键形成了1D链以及2D和3D网络结构。热重(TGA)结果表明其热稳定性与晶体氢键的强度以及强氢键的数目密切相关。并进一步探讨了此类柔性羧酸和刚性羧酸与PIPO和DACH所形成的各种超分子结构的异同，丰富了相关晶体工程的研究。
Analogous diazamesocycles 1,4-diazacycloheptane (DACH) and piperazine (PIPO) bases were rationally chosen to crystallize with a range of organic acids (including aromatic and alkyl carboxylic acids), affording two series of binary charge-assistant co-crystals, which are characterized and structurally dicussed in this work.
In chapterⅡ, sixteen diamine carboxylate are synthesized through self-assembly of DACH or PIPO with multiple carboxylic acids. The resultant compounds are as follows: [H_2DACH]·[OA](1a), [H_2PIPO]·[OA]·H_2O(1b), [H_2DACH]·[FA] (2a), [H_2PIPO]·[FA] (2b), [H_2DACH]·[TA] (3a), [H_2PIPO]·[TA](3b), [H_2DACH]·[PNA]_2 (4a), [H_2PIPO]·[PNA]_2(4b), [H_2DACH]·[NDA]·3H_2O(5a-1), [H_2DACH]·[HNDA]_2·(H_2O)·(CH_3OH) (5a-2), [H_2PIPO]·[NDA]·H_2O (5b), [H_2DACH]·[HTMA]·H_2O(6a), [H_2PIPO]·[H_2TMA]_2(6b), [H_2DACH]_2·[BTA]·2.5H_2O (7a-1), [H_2DACH]_2·[BTA]·4.5H_2O (7a-2), and [H_2PIPO]_2·[BTA]·6.5H_2O (7b). All the prepared co-crystals have a common feature of the occurrence of the proton-transfer between acid and base. Strong N-H...O interactions are involved in these co-crystals, undoubtedly following the best donor/acceptor guidelines.
And in chapterⅢ, four PIPO related compounds are obtained under general conditions. they are [(H_2PIPO)·(HBTC)] (17), [(H_2PIPO)·(HA)] (18), [(H_2PIPO)·(HCA)·H_2O] (19), [(H_2PIPO)·(PA)·3H_2O] (20). Proton-transfer has also been detected in these compounds.
X-ray single-crystal diffraction studies reveal that the stronger N-H...O and O-H...O interactions, are the driving forces for the construction of the hydrogen-bonding networks in these compounds. Thus, 1D chain structure, 2D framework and 3D framework are constructed in these compounds by multiple hydrogen bonds. Thermogravimetric analysis (TGA) of mass loss for twenty compounds has been measured in this work. The similarity in motifs of aromatic or alkyl dicarboxylic acid with DACH and PIPO functional groups is extended to synthons for prospering crystal engineering.
引文
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(2) (a) Green, B. S.; Schmidt, G. M. J. Israel Chemical Society Annual Meeting Abstracts 1971,197. (b) Cohen, M. D.; Schmidt, G M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000. (c) Schmidt, G M. J.; J. Chem. Soc. 1964, 2014.
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(4) (a) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629; (b) Nattinen, K. I.; Rissanen, K. Cryst. Eng. Commun. 2003, 5, 326; (c) Braga, D.; Maini, L.; Polito, M.; Scaccianoce, L.; Cojazzi, G.; Grepioni, F. Coord. Chem. Rev. 2001, 216, 225; (d) Mohanta, S.; Lin, H.-H.; Lee, C.-J.; Wei, H.-H. Inorg. Chem. Commun. 2002, 5, 585; (e) Koner, R.; Nayak, M.; Ferguson, G; Low, J. N.; Glidewell, C.; Misra, P.; Mohanta, S. CryEngComm. 2005, 7,129.
(5) (a) G R. Desiraju, CrystEngComm 2003,5, 466. (b) J. D. Dunitz, CrystEngComm 2003, J, 506.
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(8) Other intermolecular forces such as py.. .iodo will also be included.
(9) Aakeroy, C. B.; Beatty, A. M. Aust. J. Chem. 2001,54, 409.
(10) Burrows, A. D. Struct. Bonding 2004,108,55.
(11) (a) Etter, M. C. Acc. Chem. Res. 1990, 23, 120; (b) Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D.Acc. Chem. Rev.2001,34,107.
(12)Taylor, R.; Kennard, O.J.Am. Chem. Soc. 1982,104, 5063.
(13) Beatty, A. M. Coord. Chem. Rev. 2003,246,131.
(14) Sharma, C. V. K. Cryst. Growth Des. 2002,2, 465.
(15) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001,101,1629.
(16) Batten, S. R.; Robson, R. Angew. Chem. Int. Ed. 1998,37,1460.
(17) For recent reviews covering crystal engineering involving MOFs, see: (a) Brammer, L. Chem. Soc. Rev. 2004, 33, 476. (b) Janiak, C. Dalton Trans. 2003, 2781. (c) James, S. Chem. Soc. Rev. 2003, 32, 276. (d) Khlobystov, A. N.; Blake, A. J.; Champness, N. R.; Lemenovskii, D. A.; Majouga, A. G; Zyk, N. V.; Schroder, M. Coord. Chem. Rev. 2001, 222,155.
(18) Robson, R. J. Chem. Soc, Dalton Trans. 2000, 3735.
(19) For examples: (a) Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994,116,1151. (b) Venkataraman, D.; Moore, J. S.; Lee, S. Nature 1995,374, 792. (c) Xiong, R.-G; You, X.-Z.; Abrahams, B. F.; Xue, Z.; Che, C.-M.Angew. Chem., Int. Ed. 2001, 40, 4422. (d) Kesanli, B; Lin, W. Coord. Chem. Rev. 2003, 246, 305 and references therein, (e) Rosi, N. L.; Eckert, J.; Eddaoudi, M.; Vodak, D. T.; Kim, J.; O'Keeffe, M.; Yaghi, O. M. Science 2003,300,1127 and references therein.
(20) (a) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311. (b) Steiner, T. Angew. Chem., Int. Ed. 2002,41, 48.
(21) (a) Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D.Acc. Chem. Res. 2001,34, 107. (b) Aakeroy, C. B.; Beatty, A. M.Aust. J. Chem. 2001,54,409. (c) Walsh, R. D. B.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodrignez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003,186.
(22) (a) Burrows, A. D. Struct. Bonding 2004,108, 55. (b) Braga, D.; Maini, L.; Polito, M.; Grepioni, F. Struct. Bonding 2004,111,1.
(23) (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000. (c) Bond, A. D.; Jones, W. Supramolecular Organization and Materials Design, Cambridge University Press: Cambridge, 2002.
(24) Desiraju, G. R.Acc. Chem. Res. 2002,35,565.
(25) (a) Pedireddi, V. R.; Jones, W; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996,997. (b) Ranganathan, A.; Chatterjee, S.; Pedireddi, V. R. Tetrahedron Lett. 1998, 39, 9831. (c) Arora, K. K.; Pedireddi, V. R. J. Org. Chem. 2003,68, 9177.
(26) (a) Kuppers, H. Cryst. Struct. Commun. 1981, 10, 989. (b) Ermer, O.; Lindenberg, L. Chem. Ber. 1990, 123, 1111. (c) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J.Angew. Chem., Int. Ed. 1999,38, 381.
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