Paper
RSC Advances
for a total of 32 scans. To evaluate and compare the efficiency of 11 K. E. Uhrich, E. Reichmanis and F. A. Baiocchi, Chem. Mater.,
the different PAGs in the solid state, the epoxy polymerization
degree for each PAG/sol–gel matrix system was assessed by
1994, 6, 295–301; F. M. Houlihan, A. Shugard, R. Gooden and
E. Reichmanis, Macromolecules, 1988, 21, 2001–2006.
collecting progressive FT-IR spectra with increasing UV expo- 12 F. Ortica, C. Coenjarts, J. C. Scaiano, H. Liu, G. Pohlers and
sure time (1–18 min); the area under the bands at 3000–3060 J. F. Cameron, Chem. Mater., 2001, 13, 2297–2304.
cmꢀ1, related to C–H stretching in the epoxy ring, was calcu- 13 (a) M. De Carolis, S. Protti, M. Fagnoni and A. Albini, Angew.
lated by a Gaussian peak tting procedure (Microcal Origin
soware).
Chem., Int. Ed., 2005, 44, 1232–1236; (b) M. Ikbal, A. Jana,
N. D. P. Singh, R. Banerjee and D. Dhara, Tetrahedron,
2011, 67, 3733–3742.
14 L. L. Hench and J. K. West, Chem. Rev., 1990, 90, 33–72;
C. Sanchez, B. Lebeau, F. Ribot and M. In, J. Sol-Gel Sci.
Technol., 2000, 19, 31–38.
Acknowledgements
S.P. acknowledges MIUR, Rome (FIRB-Futuro in Ricerca 2008 15 G. Brusatin and G. Della Giustina, J. Sol-Gel Sci. Technol.,
project RBFR08J78Q) for nancial support and Prof. A. Albini 2011, 60, 299–314.
(University of Pavia) and Prof. P. Hoggard (Santa Clara Univer- 16 E. Abitelli, S. Protti, M. Fagnoni and A. Albini, J. Org. Chem.,
sity) for fruitful discussions. This work has been supported by
the Fondazione Cariplo (grant no. 2012-0186).
2012, 77, 3501–3507.
17 S. Crespi, D. Ravelli, S. Protti, A. Albini and M. Fagnoni,
Chem.–Eur. J., 2014, 20, 17572–17578.
18 Z.-Y. Tang and Q.-S. Hu, J. Am. Chem. Soc., 2004, 126, 3058–
3059.
19 B. Alonso, D. Massiot, F. Babonneau, G. Brusatin, G. Della
Giustina, P. Innocenzi and T. Kidchob, Chem. Mater., 2005,
17, 3172–3180.
Notes and references
1 R. Ayothi, Y. Yi, H. B. Cao, W. Yueh, S. Putna and C. K. Ober,
Chem. Mater., 2007, 19, 1434–1444; S.-Y. Moon and
J.-M. Kim, J. Photochem. Photobiol., C, 2007, 8, 157–173; 20 A signicant amount of formate ion, up to 2 mg Lꢀ1 was
M. Shirai and M. Tsunooka, Bull. Chem. Soc. Jpn., 1998, 71,
observed, probably due to the degradation of G8Ge2.
2483–2507; M. Shirai and M. Tsunooka, Prog. Polym. Sci., 21 G. Della Giustina, G. Brusatin, M. Guglielmi and
´
1996, 21, 1–45; J. M. Frechet, Pure Appl. Chem., 1992, 64,
1239–1248.
F. Romanato, Mater. Sci. Eng., C, 2007, 27, 1382–1385.
22 J. L. Stratenus and E. Havinga, Recl. Trav. Chim. Pays-Bas,
1966, 85, 434–436.
2 J. V. Crivello, J. Polym. Sci., Part A: Polym. Chem., 1999, 37,
4241–4254.
23 C. Raviola, V. Canevari, S. Protti, A. Albini and M. Fagnoni,
Green Chem., 2013, 15, 2704–2708.
24 H. Qrareya, S. Protti and M. Fagnoni, J. Org. Chem., 2014, 79,
11527–11533.
3 K. L. Covert and D. J. Russell, J. Appl. Polym. Sci., 1993, 49,
657–671.
´
4 J. Lalevee, X. Allonas, J.-P. Fouassier, M. Shirai and
M. Tsunooka, Chem. Lett., 2003, 32, 178–179.
5 (a) J. P. Malval, S. Suzuki, F. M. Savary, X. Allonas,
J. P. Fouassier, S. Takahara and T. Yamaoka, J. Phys. Chem.
25 C. Coenjarts, F. Ortica, J. Cameron, G. Pohlers, A. Zampini,
D. Desilets, H. Liu and J. C. Scaiano, Chem. Mater., 2001,
13, 2305–2312.
A, 2008, 112, 3879–3885; (b) M. Shirai, T. Yatsuo and 26 L. Johnstonn, N. Mathivan, F. Negri and W. Siebrand, Can. J.
M. Tsunooka, J. Photopolym. Sci. Technol., 1996, 9, 273–276;
(c) M. Shirai and H. Okamura, Prog. Org. Coat., 2009, 64,
175–181; (d) L. Steidl, S. J. Jhaveri, R. Ayothi, J. Sha,
Chem., 1993, 71, 1655–1662; D. Shukla, N. P. Schepp,
N. Mathivan and L. J. Johnston, Can. J. Chem., 1997, 75,
1820–1829.
J. D. McMullen, S. Y. C. Ng, W. R. Zipfel, R. Zentel and 27 See for example: Y. Kageyama, R. Ohshima, K. Sakurama,
C. K. Ober, J. Mater. Chem., 2009, 19, 505–513.
6 M. Ikbal, R. Banerjee, S. Atta, A. Jana, D. Dhara, A. Anoop and
N. D. P. Singh, Chem.–Eur. J., 2012, 18, 11968–11975 and
references therein.
Y. Fujiwara, Y. Tanimoto, Y. Yamada and S. Aoki, Chem.
Pharm. Bull., 2009, 57, 1257–1266; I. F. Molokov,
Y. P. Tsentalovich, A. V. Yurkovskaya and R. Z. Sagdeev, J.
Photochem.
Photobiol.,
A,
1997,
110,
159–165;
7 M. Terpolilli, D. Merli, S. Protti, V. Dichiarante,
M. Fagnoni and A. Albini, Photochem. Photobiol. Sci.,
2011, 10, 123–127.
A. K. Zarkadis, V. Georgakilas, G. P. Perdikomatis,
A. Trifonov, G. G. Gurzadyan, S. Skoulika and
M. G. Siskosa, Photochem. Photobiol. Sci., 2005, 4, 469–480.
8 D. Ravelli and M. Fagnoni, in CRC Handbook of Organic 28 M. Takezaki, N. Hirota and M. Terazima, J. Phys. Chem. A,
Photochemistry and Photobiology, ed. A. Griesbeck, M.
1997, 101, 3443–3448.
Oelgemoeller and F. Ghetti, CRC Press, 3rd edn, 2012, pp. 29 See for instance G. M. Coppinger and E. R. Bell, J. Phys.
393–417 and references therein.
9 G. G. Barclay, D. R. Medeiros and R. F. Sinta, Chem. Mater.,
1995, 7, 1315–1324.
Chem., 1966, 70, 3479–3489; M. M. Miranda and
F. Galindo, in Photochemistry of Organic Molecules in
Isotropic and Anisotropic Media, ed. V. Ramamurthy and K.
S. Schanze, Marcel Dekker Inc., New York-Basel, 2003.
10 F. M. Houlihan, T. X. Neenan, E. Reichmanis,
J. M. Kometani, L. F. Thompson, T. Chin and 30 (a) M. Gohdo, T. Takamasu and M. Wakasa, Phys. Chem.
´
O. Nalamasu, J. Photopolym. Sci. Technol., 1990, 3, 259–273.
Chem. Phys., 2011, 13, 755–761; (b) M. C. Jimenez,
This journal is © The Royal Society of Chemistry 2015
RSC Adv., 2015, 5, 33239–33248 | 33247