Zr M(Et) 4 (M) 1) Zr +0.65, Zr Zr ph7 M(Et) 4 1) l/mol/s l/mol/s 4 4, 6 Zr 4, 6, 8, Zr 1) J. D. Wright and
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2 Zr M(Et) 4 (M) 1) Zr +0.65, Zr Zr ph7 M(Et) 4 1) l/mol/s l/mol/s 4 4, 6 Zr 4, 6, 8, Zr 1) J. D. Wright and N. A. J. M. Sommerdijk, Sol-Gel Materials Chemistry and Applications, Golden and Breach Science Publishers, pp
3 Et Pr i Et Et Pr i Pr i Et Pr i (Et) 4 (Pr i ) 4 Pr i Pr i Zr i Pr Pr i Zr(Pr i ) Pr i Pr i Pr i Pr i H Zr Pr i Pr i Zr Pr i Pr i H Pr i Pr i Zr(Pr i ) 4 Pr i H H 2 H 2 H 2 H 2 H Zr H 2 H H 2 Zr 2 H H H H 2 H H H Zr H 2 H H 2 Zr 2 H H H 2 2 H 2 H H 2 2 Zr(H) 8 (H 2 ) RX 3 R=H, Alkyl, Alkenyl, Aryl, Et X=Cl, Me, Et, NC X (R 3/2 ) n R X R R X X n, X n R R R R R R R R R=Me, Vinyl, X=NC, Cl n=2 or 4 R=H, Alkyl, Alkenyl, Aryl, Cl, Me, Me 3, NR 4 Gels Linear or cyclic Cubic Ladder Ladder-like
 13 (Et) 5 V. W. Day, T. A. Eberspacher, W. G.](/docs-images/89/100515643/images/4-1.jpg "Klemperer, and C. W. Park, J. Am. Chem. Soc.")
4 (Pr i H ) 2 / Pr i H 4 α [ ](Pr i 1 -[ ](Pr i EtH ) 16 ) 13 (Et) 5 α 1 -[ ](Pr i ) 16 [ ](Pr i ) 13 (Et) 5 V. W. Day, T. A. Eberspacher, W. G. Klemperer, and C. W. Park, J. Am. Chem. Soc., 1993, 115, H Zr(R) 2 / RH 4 Zr 13 8 (Me) 36 Zr 13 8 (CH 3 ) 36 B. Morosin, Acta Cryst., 1977, B33,
 10 [Zr 13 8 ](Me) x (H) 36-x [Zr 13 8 ](Me) x (H) 36-x V. W. Day, W. G. Klemperer, and M. M. Pafford, Inorg.](/docs-images/89/100515643/images/5-0.jpg "Chem., 2005, 44, 5397-5404.")
![(1) Cl 3 H 4 dptah/ Na 2 C 3 Na 2 [ 2 (µ-dpta) 2 ] (ph 5) Na 2 H 2 [{ 4 (µ-) 4 } 2 (µ-dpta) 4 ] (ph 3) Na 2 [ 2 (µ-dpta) 2 ]](/docs-images/89/100515643/images/5-1.jpg "2-hydroxypropane-1,3-diamine-N,N,N,N -tetraacetic acid H H H N H N H (H 4 dptah) Na 2 H 2 [{ 4 (µ-) 4 } 2 (µ-dpta) 4 ] Y.")
5 H 2 / PrH Zr(Pr) 4 [Zr 3 ](Pr n MeH ) 10 [Zr 13 8 ](Me) x (H) 36-x [Zr 13 8 ](Me) x (H) 36-x V. W. Day, W. G. Klemperer, and M. M. Pafford, Inorg. Chem., 2005, 44, (1) Cl 3 H 4 dptah/ Na 2 C 3 Na 2 [ 2 (µ-dpta) 2 ] (ph 5) Na 2 H 2 [{ 4 (µ-) 4 } 2 (µ-dpta) 4 ] (ph 3) Na 2 [ 2 (µ-dpta) 2 ] 2-hydroxypropane-1,3-diamine-N,N,N,N -tetraacetic acid H H H N H N H (H 4 dptah) Na 2 H 2 [{ 4 (µ-) 4 } 2 (µ-dpta) 4 ] Y. Miyashita, Md. M. Islam, N. Amir, K. Fujisawa, and K. kamoto, Chem. Lett., 2004, 33,
6 (2) Citric acid/ Pr i H (Pr i H 2 ) (citrate) 4 (H 2 ) 12 14H 2 3HPr i 8 10 (citrate) 4 (H 2 ) 12 14H 2 3HPr i 8 14 cage structure T. Kemmitt, N. I. Al-Salim, G. J. Gainsford, A. Bubendorfer, and M. Waterland, Inorg. Chem., 2004, 43,
7 R Pr i R Pr i Pr i R Pr i R (R = (Bu t ) 3 ) Cp Cp Cp Zr Cp Zr Y. Abe and I. Kijima, Bull. Chem. Soc. Jpn., 43, 466 (1970) J. F. Harrod, et. al., Inorg. Chem., 33, 1292 (1994) L L (L = THF, Dioxane) D. Hoebbel, et. al., J. Mater. Chem., 8, (1998) K. A. Andrianov,et. al., Zh. bshch. Khim., 46, 1533 (1976): K. A. Andrianov,et. al., Izv. Akad. Nauk SSSR Ser. Khim., 10, 2314 (1977). M. B. Hursthouse and M. A. Hossain,. Polyhedron, 3, 95 (1984) R X M X M R X M R M R X (M =, Al) (R = N(Me 3 )Mes) (X = Alkyl, Cp) X X M R X M M X R M X X (M = Ga, In, Al) (R = N(Me 3 )Mes) (X = Alkyl) R. Murugavel, V. Chandrasekhar, H. W. Roesky, Acc. Chem. Res., 29, (1996).
8 Cl Bu t Bu t M M Cl Cl M Bu t Bu t M Cl F. Q. Liu, H. G. Schmidt, M. Noltemeyer, C. Freire-Erdbruegger, G. M. Sheldrick, H. W. Roesky, Zeit. Natur., B: Chem. Sci., 47, (1992). F. Q. Liu, H. G. Schmidt, M. Noltemeyer, C. Freire-Erdbruegger, G. M. Sheldrick, H. W. Roesky, Zeit. Natur., B: Chem. Sci., 47, (1992). Cl M M (M=Zr, Hf) R. Murugavel, V. S. Shete, K. Baheti, P. Davis, J. rganometal. Chem, 625, (2001). J. F. Harrod, et. al., Inorg. Chem., 33, 1292 (1994) R 1 Pr i 2 H H + 2 M Pr i R 2 R 1 R 2 M M R 1 R 2 R 1 =R 2 =Bu t, M=: Yield: 85 %. Mp: o C (Decomp.). IR 1590 (ν C= ), 1530 (ν C=C ), 1000 (ν --C ), 960 (ν -- ) (cm -1 ); 1 H NMR δ=1.3 (9H, t, -Bu t ), 2.0 (6H, d, C-CH 3 ), 5.5 (1H, s, -CH=); 13 C NMR δ=25.3 (CH 3 C-), 26.8 (CH 3 C-), 31.6 ((CH 3 ) 3 C-), 71.7 ((CH 3 ) 3 C-), (-CH=), (CH 3 C-) (CH 3 C-); 29 NMR δ= : Found:, 6.1;, 10.5 %. Calcd for C 36 H :, 6.2;, 10.6 %. R 1 =R 2 =Bu t, M=Zr: Yield: 97 %. Mp: o C (Decomposition). IR 1590 (ν C= ), 1530 (ν C=C ), 1010 (ν --C ), 970 (ν --Zr ) (cm -1 ); 1 H NMR δ=1.3 (9H, s, -Bu t ), 2.0 (6H, s, C-CH 3 ), 5.6(1H, s, -CH=); 13 C NMR δ=26.5 (CH 3 C-), 31.5 ((CH 3 ) 3 C-), 71.0 ((CH 3 ) 3 C-), (-CH=), (CH 3 C-); 29 NMR δ= Found:, 5.6; Zr, 18.4 %. : Calcd for C 36 H Zr, 5.7; Zr, 18.4 %.
9 R 1 R 1 2 H H + 2 R 2 R 2 Pr i Pr i M R 1 R 2 R 1 R 2 M M R 2 R 1 R 1 R 2 R 1 =Me, R 2 =Bu t, M=: Yield: 82.1%. Mp (Decomp.). IR 2970, 1590, 1530, 1280, 1020, 1050, 990, 970 (cm -1 ); 1 H NMR (400 MHz) δ= 0.10 (s, 12H), 1.28 (s, 36H), 2.00 (s, 24H), 5.60 (s, 4H); 13 C NMR (100.6 MHz) δ= (s), 25.4 (s), 26.9 (s), 31.6 (s), 72.7 (s), (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). MS m/z 1052 (M + ). Found:, 10.5%. Calcd. for C 40 H :, 10.6%. R 1 =R 2 =Bu t, M=: Yield: 81.9%. Mp (Decomp.). IR 2970, 1580, 1530, 1070, 1020, 960 (cm -1 ); 1 H NMR (400 MHz) δ= 1.31 (s, 72H), 1.99 (s, 24H), 5.63 (s, 4H); 13 C NMR (100.6 MHz) δ= 25.4 (s), 26.8 (s), 31.3 (s), 72.5 (s), (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). MS m/z 1211 (M + -73). Found:, 8.5%. Calcd. for C 52 H :, 8.5%. R 1 =Bu t, R 2 =Pr i, M=: Yield: 72.3%. Mp (Decomp.). IR 2977, 1708, 1592, 1106, 1070, 970 (cm -1 ); 1 H NMR (400 MHz) δ= 1.22 (s, 24H), 1.34 (s, 36H), 1.99 (s, 24H), 4.29 (s, 4H) 5.99 (s, 4H); 13 C NMR (100.6 MHz) δ= 23.9 (s), 25.4 (s), 26.8 (s), 31.6 (s), 65.9 (s), 74.6 (s), (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). VP Mn Found:, 9.2%. Calcd. for C 48 H :, 9.2%. R 1 =Me, R 2 =Bu t, M=Zr: Yield: 78.1%. Mp (Decomp.). IR 2970, 1590, 1530, 1280, 1010, 1040, 990, 950 (cm -1 ); 1 H NMR (400 MHz) δ= 0.09 (s, 12H), 1.29 (s, 36H), 1.96 (s, 24H), 5.61 (s, 4H); 13 C NMR (100.6 MHz) δ= (s), 26.9 (s), 31.5 (s), 72.7 (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). MS m/z 1123 (M + -15). Found:, 9.8%. Calcd. for C 40 H Zr 2 :, 9.8%. R 1 =R 2 =Bu t, M=Zr: Yield: 85.5%. Mp (Decomp.). IR 2970, 1600, 1530, 1070, 1020, 920 (cm -1 ); 1 H NMR (400 MHz) δ= 1.32 (s, 72H), 1.99 (s, 24H), 5.50 (s, 4H); 13 C NMR (100.6 MHz) δ= 26.7 (s), 31.5 (s), 71.5 (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). MS m/z 1297 (M + -73). Found:, 8.1%. Calcd. for C 52 H Zr 2 :, 8.1%. R 1 =Bu t, R 2 =Pr i, M=Zr: Yield: 70.5%. Mp (Decomp.). IR 2981, 1710, 1592, 1105, 970, 916 (cm -1 ); 1 H NMR (400 MHz) δ= 1.21 (s, 24H), 1.34 (s, 36H), 1.97 (s, 24H), 4.31 (s, 4H) 5.98 (s, 1H); 13 C NMR (100.6 MHz) δ= 25.6 (s), 26.6 (s), 31.6 (s), 65.8 (s), 73.9 (s), (s), (s); 29 NMR (79.5 MHz) δ= (s). VP Mn Found:, 8.4%. Calcd. for C 48 H Zr 2 :, 8.5%. R 1 R 1 2 H H + 2 R 2 R 2 Pr i Pr i M R 1 R 2 R 1 R 2 M M R 2 R 1 R 1 R 2 R 1 =R 2 =, M=: Yield: 85.2%. Mp (Decomp.). IR 3060, 2970, 1580, 1530, 1130, 1015, 940 (cm -1 ); 1 H NMR (400 MHz) δ= 1.84 (br, 24H), 5.61 (s, 4H), 7.25 (m, 40H); 13 C NMR (100.6 MHz) δ= 24.9 (s), 25.8 (s), (d), (q), (s), (s); 29 NMR (79.5 MHz) δ= (s). MS m/z 1273 (M + -43). Found:, 8.4%. Calcd. for C 68 H :, 8.5%. R 1 =R 2 =, M=Zr: Yield: 96.1%. Mp (Decomp.). IR 3060, 2970, 1580, 1530, 1120, 1015, 930 (cm -1 ); 1 H NMR (400 MHz) δ= (m, 24H), 5.63 (t, 4H), 7.23 (m, 40H); 13 C NMR (100.6 MHz) δ= 26.3 (s), 26.7 (s), (d), (q), (s), (s); 29 NMR (79.5 MHz) δ= (s), (s). MS m/z 1402 (M + ). Found:, 7.9%. Calcd. for C 68 H Zr 2 :, 8.0%.
10 2 H H + 2 Cl Cl R R R n (Bu t ) 3 H + (n=2, 3) (Pr i ) 4 [(Bu t ) 3 ] n (Pr i ) 4-n TS2 (n=2), TS3 (n=3) R=Cl (CTS-Cl): Yield: 88 %. Mp: 218 o C (Decomp.). IR 3067 (ν C-H ), 1123 (ν -C ), 942 (ν -- ), 818 (ν -Cl ) (cm -1 ); 1 H NMR δ=6.28 (s, 10H, Cp-H), (m, 20H, Ar-H); 13 C NMR δ=118.3 (-Cp), (-), (-), (-), (-); 29 NMR δ= R=Cp (CZS-Cp): CZS-Cp: Yield: 77 %. Mp: 182 o C (Decomp.). IR 3066 (ν C-H ), 1118 (ν -C ), 939 (ν --Zr ) (cm -1 ); 1 H NMR δ=6.09 (m, 20H, Cp-H), (m, 20H, Ar-H); 13 C NMR δ=113.0 (Zr-Cp), (-), (-), (-), (-); 29 NMR δ= R=Cp (CTS-Cp): : Yield: 93 %. Mp: o C (Decomp.). IR 3055 (ν C-H ), 1428 (ν C=C ),1122 (ν -C ), 947 (ν -- ) (cm -1 ); 1 H NMR δ= (m, 20H, Cp-H), (m, 20H, Ar-H); 13 C NMR δ=118.8 (-Cp), (-Cp), (-), (-), (-), (-); 29 NMR δ= Bu t Bu t Zr Zr Bu t But
11 Bu t Bu t Bu t But CTS CZS
12 [(Bu t ) 2 (acac) 2 ] 2 CTS [(Bu t ) 3 ] n (Pr i ) 4-n TS2 (n=2), TS3 (n=3) 2-2 n 2-2 Table Crystal form a) and the average crystallite size b) of CTS, TS2, and TS3 on pyrolysis Temp./ CTS TS2 TS3 o C Form ze/ A Form ze/ A Form ze/ A A A 39 A A 72 A 54 A A+R 121 A 78 A A+R 217 A+R 155 A 109 a) -: Amorphous, A: Anatase, R: Rutile b) Calculated from the Scherrer's equation. Cristalline size/ Å CTS TS2 TS3 Temp/ o C Crystal size of 2 anatase on heat-treatment [(Bu t ) 2 (acac) 2 ] 2 CTS 2-2 Table loxane units of CTS on pyrolysis a) Temperature/ loxane unit (%) o C Q 3 Q 3 Q a) Calculated from 29 DD/MAS NMR after deconvolution. 29 DD/MAS NMR spectra of CTS after heat-treatment Deconvoluted 29 DD/MAS NMR spectra
13 R R R R R R R R R R R R R R R R R R R R R R R R Q 3 2 H Q 4 Q 3 H Q 3 H Q 4 Scheme 1 A model for the rearrangement of CTS on pyrolysis. Temperature ( o C) R acac Bu t Bu t Bu t (H) m-2 2 acac acac acac acac 2 2 R=Vi R=Pr i (Et) 4-m acac n x Molar fraction (mol%) ((Bu t ) 3 ) n (Pr i ) 4-n 2
14 (Et) 4 + M(Pr i ) 4 TES TPT, TPZ (M=, Zr) H 2 (as a saturated vapor) R R x R M R PTS (A), PZS (A) (R=Et, Pr i, H) y HCl/ H M(Pr i 2 ) 4 (Et) 4 (Et) 4-n (H) n TES TPT, TPZ (M=, Zr) R R x R M R PTS (B), PZS (B) (R=Et, Pr i, H) y R R R R L HL M M x R y R x L y PTS (A), PZS (A) PTS (B), PZS (B) APTS (A), APZS (A) (R=Et, H; L=acac) APTS (B), APZS (B) (R=Et, H; L=acac)
15 No. Polymetalla- Metal content M me/ h Yield/ % siloxane /% M/% /M c) d) M n Table Preparation of APTS(A) a) and APZS(A) b) 1 APTS(A) APZS(A) Zr 10 - e) f) a) TES: g (0.05 mol), TPT: g (0.05 mol); temp.: 24 o C. b) TES: 4.17 g (0.02 mol), TPZ: 7.75 g (0.02 mol); benzene: 10 ml; temp.: 40 o C. c) Molar ratio. d) Measured by VP. e) No precipitation. f) Gelled. Table Preparation of APTS(B) a) and APZS(B) b) Polymetalla- H Metal content No. M 2 /TES d) Yield/ % M siloxane Molar ratio / % M/ % /M c) n 12 APTS(B) APZS(B) Zr a) TES: 4.17 g (0.02 mol), TPT: 5.68 g (0.02 mol); ethanol: 40 ml; 2-propanol: 20 ml; HCl/TES molar ratio: 0.1. b) TES: 4.17 g (0.02 mol), TPZ: 7.75 g (0.02 mol); ethanol: 100 ml; THF: 40 ml; HCl/TES molar ratio: 0.1. c) Molar ratio. d) Measured by VP. e) No precipitation. f) Gelled.
16 APTS(A) 29 NMR APTS(B) 29 NMR Table 3 Relative ratio a) of peaks Q n of polymetallasiloxanes No. Polymetallasiloxane Q 1 Percentage of silicon units b) Q 2 Q 3 Q 4 1 APTS(A) APZS(A) APTS(B) APZS(B) a) Estimated from the results of 29 NMR spectra b) A symbol Q n denotes the microstructure of silicon atom as () n (R) 4-n.
17 APTS(A)IR APTS(B)IR R R R R 1 R 6 R (a) PTS (A) (No. 3) L M n 6 1 L 14 / bsd. (Calcd.) 3500 (3658) 1.00 (1) Q 1 /Q 2 /Q 3 /Q 4 8/43/37/11 (7/43/43/7) R R R R 1 R 1 R (b) PTS (B) (No. 13) L M n 3 2 L 7 / bsd. (Calcd.) 2200 (2282) 1.03 (1) Q 1 /Q 2 /Q 3 /Q 4 9/14/45/33 (14/14/43/29) R R R R 2 R 2 R (c) PZS (A) (No. 10) L M Zr n 3 3 L 10 /Zr bsd. (Calcd.) 3600 (3613) 1.00 (1) Q 1 /Q 2 /Q 3 /Q 4 17/23/27/33 (20/20/20/30) R R R R 1 R 1 R (d) PZS (B) (No. 16) L M Zr n 2 2 L 6 /Zr bsd. (Calcd.) 2400 (2341) 1.01 (1) Q 1 /Q 2 /Q 3 /Q 4 14/23/31/32 (17/17/33/33)
18 APTS(A) No.3 APTS(B) No.13 Table Crystal form a) and crystalline size b) of APTS(A) for Nos. 1-3 and APTS(B) for Nos on heat treatment Crystal form and crystalline size/ nm Temp./ o C APTS(A) APTS(B) No. 1 No. 2 No. 3 No. 12 No. 13 No A (36) A (39) A (36) - A (45) A (43) A (46) A (41) - A (46) A (47) A (41) A (38) 900 A (80) A (55) A (49) A (91) A (66) A (61) 1000 A (125), R A (110) A (65) A (106) A (91) A (84) 1100 A (241), R A (202), R A (144) A (212), R A (198), R A (161) 1200 R A (234), R A (271), R A (297), R A (372), R A (223), R 1300 R R A (305), R R A (411), R A (440), R 1400 R R R R R R a) -: Amorphous, A: anatase form of 2., R: rutile form of 2. b) Represented in the parentheses. Calculated from Scherrer s equation.
19 Table Crystal form a) and crystalline size b) of APZS(A) for Nos. 7, 8, and 10 and APZS(B) for Nos on heat treatment Crystal form and crystalline size/ nm Temp./ o C APZS(A) APZS(B) No. 7 No. 8 No. 10 No. 15 No. 16 No T (43) T (46) T (56) - - T (56) T (62) - - T (70) T (35) - T (46) T (70) T (37) T (32) T (83) T (55) T (49) 1000 T (74) T (63) T (62) T (101) T (70) T (56) 1100 T (112) T (96) T (86) T (112) T (86) T (82) 1200 T (223) T (186) T (159) T (207) T (169) T (159) a) -: Amorphous, T: tetragonal Zr 2. b) Represented in the parentheses. Calculated from Scherrer s equation.
20 Pr i L Zr L Pr i EZE (L=etac) H 2, HCl L Zr L PZ n Table Hydrolysis condition for EZP and spinnability of concentrated PZ methanol solution. H 2 /EZP Molar ratio HCl/EZP me/ h a) Concentrated methanol solution (84 wt%); Hydrolysis of EZP was carriedout in MeH Spinnability b) / cm H NMR spectra of PZ in CCl 4 (a) and CDCl 3 (b) Results of the determination of EtH formed During the hydrolysis of EZE. Results of the determination of etach formed During the hydrolysis of EZE.
21 Table Analytical data for PZ and the hydrolysis products of EZE. Ethanol etach PZ formed by hydlolysis/ mol formed by hydrolysis/ mol Molecular weight (Mn) by VP Zr content/ % etac/zr molar ratio H/etac molar ratio a) Against one mole equivalent of EZE. b) Analysis: C 28.4 %, H 4.0 %. c) etac/zr=c/zr=(28.4/12.0/6)/(32.3/91.2)=1.1 d) bserved from the proton ratio of silylates by NMR. bserved Value 1.9 a) 0.72 a) b) 1.1 c) 0.6 d) Table Analytical data for the estimated structures of PZ. a) bserved Calcd. Compositions x y z w MW Elemental Analysis/ % C H Zr Molar ratio etac/zr H/etac H H L Zr Zr Zr L L Zr L L H L H Zr Zr L H Zr L L L H Zr Zr L H Zr H L a) Formula: Zr x (H) y (etac) z w Y(acac) 3 3.0Y-PZ Y 2 3 3%
22 (a) ( ) h 3.0Y-PZ (a) (b)sem ZrCl 2 8 H 2 ZC Hetac, Et 3 N MeH etac Zr H n PZ-ZC Table Results on the preparation of PZ-ZC Yield / Metal analysis a) / State % % (calcd.) 70.6 W hite powder 37.8 (36.0) a) Determined by ICP. HCH 2 CH 2 H, Et 3 N ZrCl 2 8 H 2 MeH ZC Cl CH 2 CH 2 H Zr H PZ-EG Table Results on the preparation of PZ-EG Yield / Metal analysis a) / State % % (calcd.) 95.2 White powder 41.9 (41.2) a) Determined by ICP. n
CTETS 7 8 9 11 Addition Rf Rf u Rf Rf u u : R, R 2, RS, X etc. Hydrolysisesterification Ewg Ewg H C 3 H C 2 R Ewg Ewg Ewg=C 3, C 2 R' etc. R=H or Alkyl Ewg Ewg RH Base Ewg Ewg R RH Base Ewg Ewg R R Amidation
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