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![ABSTRACT An investigation was undertaken to gain understanding of the type of bond cleavage (heterolysis _versus_ homolysis) of 1-(methoxy-substituted arylmethyloxy)-9,10-anthraquinones (1) as bichromophoric photoinitiators of styrene (St) and cyclohexene oxide (CHO) polymerization to aid development of a novel and efficient hybrid photoinitiator. Results indicated that the 4-methoxynaphthalen-1-ylmethyl-substituted photoinitiator 1 containing no halogen or metal induces radical and cationic polymerization reactions of St and CHO, respectively, to give the corresponding polymers in reasonable yields. This initiator also accomplished hybrid photopolymerization of an equimolar mixture of St and CHO, although the ability to initiate polymerization was reduced. Analysis of the photoproducts derived from specific initiators as well as of the polymer end groups substantiated that the arylmethyloxyl radical and arylmethyl carbocation are major reactive species initiating the polymerization of St and CHO, respectively. In addition, the charge-separated state characteristic of the 9,10-anthraquinon-1-yloxy chromophore in the singlet excited state played a pivotal role in the heterolytic bond-cleavage in the latter monomer. SIMILAR CONTENT BEING VIEWED BY OTHERS SILYLOXY-SUBSTITUTED ANTHRAQUINONES AS TYPE I PHOTOINITIATORS FOR VISIBLE LIGHT-INDUCED RADICAL POLYMERIZATION Article Open access 07 January 2025 ENERGY-TRANSFER-INDUCED [3+2] CYCLOADDITIONS OF N–N PYRIDINIUM YLIDES Article 26 June 2023 VISIBLE LIGHT-CONTROLLED LIVING CATIONIC POLYMERIZATION OF METHOXYSTYRENE Article Open access 24 June 2022 ARTICLE PDF REFERENCES * J. V. Crivello and K. Dietliker, in _“Photoinitiators for Free Radical, Cationic & Anionic Photopolymerisation,”_ 2nd ed., G. Bradley, Ed., John Wiley and Sons, London, 1998. Google Scholar * J. D. Oxman, D. W. Jacobs, and M. C. Trom, _Polym. Mater. Sci. Eng._, 88, 239 (2003). * F. Kasapoglu, M. Aydin, N. Arsu, and Y. Yagci, _J. Photochem. Photobiol., A_, 159, 151 (2003). * E. Takahashi, F. Sanda, and T. Endo, _J. Polym. Sci., Part A: Polym. Chem._, 41, 3816 (2003). * E. Takahashi, F. Sanda, and T. Endo, _J. Appl. Polym. Sci._, 91, 3470 (2004). * T. Hino and T. Endo, _Macromolecules_, 37, 1671 (2004). * K. Tanaka, K. Nakamura, N. Yoshioka, A. Kameyama, T. Igarashi, and T. Sakurai, _J. Polym. Sci., Part A: Polym. Chem._, 42, 2859 (2004). * J. D. Oxman, D. W. Jacobs, M. C. Trom, V. Sipani, B. Ficek, and A. B. Scranton, _J. Polym. Sci., Part A: Polym. Chem._, 43, 1747 (2005). * M.-S. Lin and M.-W. Wang, _Polym. Int._, 48, 1237 (1999). * C. Decker, T. Nguyen Thi Viet, D. Decker, and E. Weber-Koehl, _Polymer_, 42, 5531 (2001). * L. Lecamp, C. Pavillon, P. Lebaudy, and C. Bunel, _Eur. Polym. J._, 41, 169 (2005). * A. A. Al-Doaiss, W. Günther, E. Klemm, and D. Stadermann, _Macromol. Chem. Phys._, 206, 2348 (2005). * N. Yonet, N. Bicak, and Y. Yagci, _Macromolecules_, 39, 2736 (2006). * K. Tanaka, Y. Takahashi, T. Isobe, T. Satoh, R. Akimoto, T. Igarashi, and T. Sakurai, _J. Photochem. Photobiol., A_, 174, 130 (2005). * N. Yoshioka, C. Andoh, K. Kubo, T. Igarashi, and T. Sakurai, _J. Chem. Soc., Perkin Trans._ 2, 1927 (2001). * K. Tanaka, R. Akimoto, T. Igarashi, and T. Sakurai, _J. Polym. Sci., Part A: Polym. Chem._, 44, 25 (2006). * J. Gao, N. Li, and M. Freindorf, _J. Am. Chem. Soc._, 118, 4912 (1996). * K. Tanaka, Y. Koizumi, T. Igarashi, and T. Sakurai, _Macromolecules_, 39, 8556 (2006). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, Kanagawa-ku, Yokohama, 221-8686, Japan Masakazu Tozuka, Tetsutaro Igarashi & Tadamitsu Sakurai Authors * Masakazu Tozuka View author publications You can also search for this author inPubMed Google Scholar * Tetsutaro Igarashi View author publications You can also search for this author inPubMed Google Scholar * Tadamitsu Sakurai View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Tadamitsu Sakurai. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Tozuka, M., Igarashi, T. & Sakurai, T. 1-(Arylmethyloxy)-9,10-anthraquinones: Photoinitiators for Radical and Cationic Polymerizations. _Polym J_ 41, 709–714 (2009). https://doi.org/10.1295/polymj.PJ2009066 Download citation * Received: 23 March 2009 * Accepted: 24 May 2009 * Published: 09 July 2009 * Issue Date: 01 September 2009 * DOI: https://doi.org/10.1295/polymj.PJ2009066 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Initiator * Photochemistry * Cationic Polymerization * Radical Polymerization * Substituent Effect](https://media.springernature.com/w215h120/springer-static/image/art%3A10.1038%2Fs41428-024-01001-9/MediaObjects/41428_2024_1001_Figa_HTML.png)
ABSTRACT An investigation was undertaken to gain understanding of the type of bond cleavage (heterolysis _versus_ homolysis) of 1-(methoxy-substituted arylmethyloxy)-9,10-anthraquinones (1)
as bichromophoric photoinitiators of styrene (St) and cyclohexene oxide (CHO) polymerization to aid development of a novel and efficient hybrid photoinitiator. Results indicated that the
4-methoxynaphthalen-1-ylmethyl-substituted photoinitiator 1 containing no halogen or metal induces radical and cationic polymerization reactions of St and CHO, respectively, to give the
corresponding polymers in reasonable yields. This initiator also accomplished hybrid photopolymerization of an equimolar mixture of St and CHO, although the ability to initiate
polymerization was reduced. Analysis of the photoproducts derived from specific initiators as well as of the polymer end groups substantiated that the arylmethyloxyl radical and arylmethyl
carbocation are major reactive species initiating the polymerization of St and CHO, respectively. In addition, the charge-separated state characteristic of the 9,10-anthraquinon-1-yloxy
chromophore in the singlet excited state played a pivotal role in the heterolytic bond-cleavage in the latter monomer. SIMILAR CONTENT BEING VIEWED BY OTHERS SILYLOXY-SUBSTITUTED
ANTHRAQUINONES AS TYPE I PHOTOINITIATORS FOR VISIBLE LIGHT-INDUCED RADICAL POLYMERIZATION Article Open access 07 January 2025 ENERGY-TRANSFER-INDUCED [3+2] CYCLOADDITIONS OF N–N PYRIDINIUM
YLIDES Article 26 June 2023 VISIBLE LIGHT-CONTROLLED LIVING CATIONIC POLYMERIZATION OF METHOXYSTYRENE Article Open access 24 June 2022 ARTICLE PDF REFERENCES * J. V. Crivello and K.
Dietliker, in _“Photoinitiators for Free Radical, Cationic & Anionic Photopolymerisation,”_ 2nd ed., G. Bradley, Ed., John Wiley and Sons, London, 1998. Google Scholar * J. D. Oxman, D.
W. Jacobs, and M. C. Trom, _Polym. Mater. Sci. Eng._, 88, 239 (2003). * F. Kasapoglu, M. Aydin, N. Arsu, and Y. Yagci, _J. Photochem. Photobiol., A_, 159, 151 (2003). * E. Takahashi, F.
Sanda, and T. Endo, _J. Polym. Sci., Part A: Polym. Chem._, 41, 3816 (2003). * E. Takahashi, F. Sanda, and T. Endo, _J. Appl. Polym. Sci._, 91, 3470 (2004). * T. Hino and T. Endo,
_Macromolecules_, 37, 1671 (2004). * K. Tanaka, K. Nakamura, N. Yoshioka, A. Kameyama, T. Igarashi, and T. Sakurai, _J. Polym. Sci., Part A: Polym. Chem._, 42, 2859 (2004). * J. D. Oxman, D.
W. Jacobs, M. C. Trom, V. Sipani, B. Ficek, and A. B. Scranton, _J. Polym. Sci., Part A: Polym. Chem._, 43, 1747 (2005). * M.-S. Lin and M.-W. Wang, _Polym. Int._, 48, 1237 (1999). * C.
Decker, T. Nguyen Thi Viet, D. Decker, and E. Weber-Koehl, _Polymer_, 42, 5531 (2001). * L. Lecamp, C. Pavillon, P. Lebaudy, and C. Bunel, _Eur. Polym. J._, 41, 169 (2005). * A. A.
Al-Doaiss, W. Günther, E. Klemm, and D. Stadermann, _Macromol. Chem. Phys._, 206, 2348 (2005). * N. Yonet, N. Bicak, and Y. Yagci, _Macromolecules_, 39, 2736 (2006). * K. Tanaka, Y.
Takahashi, T. Isobe, T. Satoh, R. Akimoto, T. Igarashi, and T. Sakurai, _J. Photochem. Photobiol., A_, 174, 130 (2005). * N. Yoshioka, C. Andoh, K. Kubo, T. Igarashi, and T. Sakurai, _J.
Chem. Soc., Perkin Trans._ 2, 1927 (2001). * K. Tanaka, R. Akimoto, T. Igarashi, and T. Sakurai, _J. Polym. Sci., Part A: Polym. Chem._, 44, 25 (2006). * J. Gao, N. Li, and M. Freindorf, _J.
Am. Chem. Soc._, 118, 4912 (1996). * K. Tanaka, Y. Koizumi, T. Igarashi, and T. Sakurai, _Macromolecules_, 39, 8556 (2006). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS *
Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, Kanagawa-ku, Yokohama, 221-8686, Japan Masakazu Tozuka, Tetsutaro Igarashi & Tadamitsu Sakurai
Authors * Masakazu Tozuka View author publications You can also search for this author inPubMed Google Scholar * Tetsutaro Igarashi View author publications You can also search for this
author inPubMed Google Scholar * Tadamitsu Sakurai View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Tadamitsu
Sakurai. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Tozuka, M., Igarashi, T. & Sakurai, T. 1-(Arylmethyloxy)-9,10-anthraquinones:
Photoinitiators for Radical and Cationic Polymerizations. _Polym J_ 41, 709–714 (2009). https://doi.org/10.1295/polymj.PJ2009066 Download citation * Received: 23 March 2009 * Accepted: 24
May 2009 * Published: 09 July 2009 * Issue Date: 01 September 2009 * DOI: https://doi.org/10.1295/polymj.PJ2009066 SHARE THIS ARTICLE Anyone you share the following link with will be able to
read this content: Get shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing
initiative KEYWORDS * Initiator * Photochemistry * Cationic Polymerization * Radical Polymerization * Substituent Effect