Preparation and characterization of single crystals of tetrakis(4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)phenyl)germane

Tae Won Lee; Dong Woo Lee; Yeonjeong Choi; Kang Min Ok; Kwangyong Park

Journal of Industrial and Engineering Chemistry, Vol.69, 444-448, January, 2019

DOI10.1016/j.jiec.2018.09.024 Export Citation

Preparation and characterization of single crystals of tetrakis(4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)phenyl)germane

Tae Won Lee, Dong Woo Lee¹, Yeonjeong Choi, Kang Min Ok^{1, †}, and Kwangyong Park^†

School of Chemical Engineering and Materials Science, Chung-Ang University, Seoul, 06974, Republic of Korea
¹Department of Chemistry, Chung-Ang University, Seoul, 06974, Republic of Korea

E-mail:,

A novel tetrakis(4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2- yl)phenyl)germane (2) was synthesized by the reaction of germanium(IV) tetrachloride with 4-(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)phenyllithium. Colorless plate-shaped single crystals obtained from recrystallization in ether were characterized by the single-crystal X-ray diffraction. The organogermanium compound was crystallized in a noncentrosymmetric nonpolar tetragonal space group, I-4, and classified as a porous molecular material owing to the presence of two types of distinct channels as a result of intermolecular hydrogen bonding. Compound 2 exhibits a differential gas adsorption property. The powder second-harmonic generating (SHG) measurements indicate that compound 2 shows a SHG efficiency 10 times greater than those of α-SiO2 and type-1 nonphase-matchable.

Keywords:Organogermanium compound;Single crystal;Tetrahedral;Gas adsorption;Second-harmonic generating efficiency

[References]

Kjelstrup-Hansen J, Norton JE, Silva Filho DA, Bredas JL, Rubahn HG, Org. Electron., 10, 1228 (2009)
Kumar S, Singh P, Srivastava R, Ghosh S, RCS Adv., 5, 61249 (2015)
Cappelli A, Razzano V, Fabio G, Paolini M, Grisci G, Giuliani G, Donati A, Mendichi R, Mroz W, Villafiorita F, Botta C, RCS Adv., 5, 101377 (2015)
Shirota YJ, Mater. Chem., 15, 75 (2005)
Wang SJ, Oldham WJ, Hudack RA, Bazan GC, J. Am. Chem. Soc., 122(24), 5695 (2000)
Kim SK, Park YI, Kang IN, Park JW, J. Mater. Chem., 17, 4670 (2007)
Liu S, He F, Wang H, Xu H, Wang C, Li F, Ma Y, J. Mater. Chem., 18, 4802 (2008)
Lo SC, Burn PL, Chem. Rev., 107(4), 1097 (2007)
Furuta P, Brooks J, Thompson ME, Frechet JMJ, J. Am. Chem. Soc., 125(43), 13165 (2003)
Lyu YY, Kwak J, Jeon WS, Byun Y, Lee HS, Kim D, Lee C, Char K, Adv. Funct. Mater., 19(3), 420 (2009)
Kim CM, Yoon MJ, Hong SH, Park KY, Kim SY, Electron. Mater. Lett., 12, 388 (2016)
Spek AL, Platon, A Multi-Purpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2001.
Dybtsev DN, Chun H, Yoon SH, Kim D, Kim K, J. Am. Chem. Soc., 126(1), 32 (2004)
Maji TK, Matsuda R, Kitagawa S, Nat. Mater., 6(2), 142 (2007)
Ok KM, Sung J, Hu G, Jacobs RMJ, O'Hare D, J. Am. Chem. Soc., 130(12), 3762 (2008)
Lee HJ, Cho W, Jung S, Oh M, Adv. Mater., 21(6), 674 (2009)
Nugent PS, Rhodus VL, Pham T, Forrest K, Wojtas L, Space B, Zaworotko MJ, J. Am. Chem. Soc., 135, 10950 (2013)
Lee NH, Lee DW, Yeo H, Kwak K, Chun HS, Ok KM, CrystEngComm, 16, 5619 (2014)
Steele W, Chem. Rev., 93, 2355 (1993)
Kurtz SK, Perry TT, J. Appl. Phys., 39, 3798 (1968)
SAINT, Program for Area Detector Absorption Correction, version 4.05, Siemens Analytical X-ray Instruments, Madison, WI, USA, 1995.
Blessing RH, Acta Crystallogr. A, 51, 33 (1995)
Sheldrick GM, SHELXS-97, A Program for Automatic Solution of Crystal Structures, University of Goettingen, Goettingen, Germany, 1997.
Sheldrick GM, SHELXL-97, A Program for Crystal Structure Refinement, University of Goettingen, Goettingen, Germany, 1997.
Farrugia LJ, J. Appl. Crystallogr., 32, 837 (1999)
Kurtz SK, Perry TT, J. Appl. Phys., 39, 3798 (1968)
Ok KM, Chi EO, Halasyamani PS, Chem. Soc. Rev., 35, 710 (2006)

[1] Kjelstrup-Hansen J, Norton JE, Silva Filho DA, Bredas JL, Rubahn HG, Org. Electron., 10, 1228 (2009)

[2] Kumar S, Singh P, Srivastava R, Ghosh S, RCS Adv., 5, 61249 (2015)

[3] Cappelli A, Razzano V, Fabio G, Paolini M, Grisci G, Giuliani G, Donati A, Mendichi R, Mroz W, Villafiorita F, Botta C, RCS Adv., 5, 101377 (2015)

[4] Shirota YJ, Mater. Chem., 15, 75 (2005)

[5] Wang SJ, Oldham WJ, Hudack RA, Bazan GC, J. Am. Chem. Soc., 122(24), 5695 (2000)

[6] Kim SK, Park YI, Kang IN, Park JW, J. Mater. Chem., 17, 4670 (2007)

[7] Liu S, He F, Wang H, Xu H, Wang C, Li F, Ma Y, J. Mater. Chem., 18, 4802 (2008)

[8] Lo SC, Burn PL, Chem. Rev., 107(4), 1097 (2007)

[9] Furuta P, Brooks J, Thompson ME, Frechet JMJ, J. Am. Chem. Soc., 125(43), 13165 (2003)

[10] Lyu YY, Kwak J, Jeon WS, Byun Y, Lee HS, Kim D, Lee C, Char K, Adv. Funct. Mater., 19(3), 420 (2009)

[11] Kim CM, Yoon MJ, Hong SH, Park KY, Kim SY, Electron. Mater. Lett., 12, 388 (2016)

[12] Spek AL, Platon, A Multi-Purpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2001.

[13] Dybtsev DN, Chun H, Yoon SH, Kim D, Kim K, J. Am. Chem. Soc., 126(1), 32 (2004)

[14] Maji TK, Matsuda R, Kitagawa S, Nat. Mater., 6(2), 142 (2007)

[15] Ok KM, Sung J, Hu G, Jacobs RMJ, O'Hare D, J. Am. Chem. Soc., 130(12), 3762 (2008)

[16] Lee HJ, Cho W, Jung S, Oh M, Adv. Mater., 21(6), 674 (2009)

[17] Nugent PS, Rhodus VL, Pham T, Forrest K, Wojtas L, Space B, Zaworotko MJ, J. Am. Chem. Soc., 135, 10950 (2013)

[18] Lee NH, Lee DW, Yeo H, Kwak K, Chun HS, Ok KM, CrystEngComm, 16, 5619 (2014)

[19] Steele W, Chem. Rev., 93, 2355 (1993)

[20] Kurtz SK, Perry TT, J. Appl. Phys., 39, 3798 (1968)

[21] SAINT, Program for Area Detector Absorption Correction, version 4.05, Siemens Analytical X-ray Instruments, Madison, WI, USA, 1995.

[22] Blessing RH, Acta Crystallogr. A, 51, 33 (1995)

[23] Sheldrick GM, SHELXS-97, A Program for Automatic Solution of Crystal Structures, University of Goettingen, Goettingen, Germany, 1997.

[24] Sheldrick GM, SHELXL-97, A Program for Crystal Structure Refinement, University of Goettingen, Goettingen, Germany, 1997.

[25] Farrugia LJ, J. Appl. Crystallogr., 32, 837 (1999)

[26] Kurtz SK, Perry TT, J. Appl. Phys., 39, 3798 (1968)

[27] Ok KM, Chi EO, Halasyamani PS, Chem. Soc. Rev., 35, 710 (2006)