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Enzymatic synthesis of furan-based polymers

Maniar, Dina

DOI:

10.33612/diss.97973091

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

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Publication date: 2019

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Maniar, D. (2019). Enzymatic synthesis of furan-based polymers. Rijksuniversiteit Groningen. https://doi.org/10.33612/diss.97973091

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Acknowledgements

Alhamdulillahirabbil’alamin, all praises for Allah

I have learned a lot in the past four years of my PhD study and it would not have been possible without the tremendous help and support that I received from many people. It is thus my great pleasure to express my appreciation for everyone who has contributed directly and indirectly to complete this thesis. First of all, I would like to thank my promotor Prof. Katja Loos. Katja, thank you for giving me the opportunity me to do PhD in your group. Your friendly nature has always been very welcoming and I do not think I know many people who is as patient as you are. After my short research project for the ITB-Zernike Master Sandwich program, I was eager/delighted to join your group and continue the work on enzymatic polymerization. Thank you for the effort and support you provided during the proposal preparation, which made it possible for me to obtain a scholarship from LPDP to undertake my PhD. I also want to thank you for entrusting me with the freedom to develop my own ideas and use my creativity in this research project. I appreciate all the valuable experiences that I gained in your research group and I am sincerely grateful for your kindness and help throughout my study. Thank you so much for your understanding to give me an extended leave of absence when I needed it, my family and I greatly appreciate it. Vielen Dank.

I sincerely thank my co-promotor Prof. Cynthia L. Radiman. Ibu Cynthia, I have learned so many great things from you and I always respect you. Thank you for all help and guidance throughout my bachelor, master and now PhD program. Thank you very much for your word of inspiration and encouragement to pursue higher education and for me to be a better person. Terima kasih banyak Bu saya sudah diantar sampai dapat gelar doktor. Semoga Tuhan YME senantiasa membalas kebaikan Ibu. I would like to thank the members of the assessment committee: Prof. Francesco Picchioni from the University of Groningen, Prof. Frank Hollmann from Delft University of Technology, and Prof.

Alessandro Gandini from the University of São Paulo, for their valuable time and effort to evaluate this thesis.

I gratefully acknowledge the scholarship received to undertake my PhD from Indonesian Endowment Fund for Education (Lembaga Pengelola Dana Pendidikan), Ministry of Finance of Republic of Indonesia.

During my PhD, I had the chance to interact and collaborate with a number of people. I want to thank Dr. Jiang; Yi, I want to thank you for your guidance and share of knowledge about this research. Thank you for helping me at the beginning of my PhD studies. I have learnt a lot from you and I really enjoyed our discussion and collaboration. Your significant contribution in this project is certainly appreciated. I always admire your determination and perseverance, very inspiring, it was a great pleasure to work with you, 謝謝. Dr. Fodor and Dr. Skoczinski, our former group members and my lab mates. Csaba, thank you for all the discussions we had and for helping me in daily basis. Especially in the beginning of my PhD, you helped me a lot with improving my skills to work in the lab. Your scientific and technical skills are incredible and I learned a lot from you. Pia, unexpectedly we have co-authored a couple of publications, thank you for our interesting discussions and collaboration. Thanks to you, now I can see enzyme in a broader point of view. Ich habbe einen schlüssel im schussel! Danke schön! Albert Woortman, Jur van Dijken and Gert Alberda van Ekenstein, talented technicians in our group. Dear Albert, I am sincerely grateful for your support in a number of ways. Your expertise and knowledge of SEC measurement undoubtedly helpful for the completion of this thesis. Thank you very much for helping me with the proof-reading of manuscripts and also translating my summary to Dutch. You are always willing to help me in any situation and give me words of encouragement, which I appreciate very much. Dank u wel. Gert and Jur, thank you for advice and help with the DSC and TGA measurement.

I had the chance to be the daily supervisor of several talented (under)graduate students. Kathi, Daniel, Indra, Señorita Viviana, and Mónica; thank you very much, it was a great pleasure to work with all of you. Thanks to your efforts, we can have fruitful

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Acknowledgements

Alhamdulillahirabbil’alamin, all praises for Allah

I have learned a lot in the past four years of my PhD study and it would not have been possible without the tremendous help and support that I received from many people. It is thus my great pleasure to express my appreciation for everyone who has contributed directly and indirectly to complete this thesis. First of all, I would like to thank my promotor Prof. Katja Loos. Katja, thank you for giving me the opportunity me to do PhD in your group. Your friendly nature has always been very welcoming and I do not think I know many people who is as patient as you are. After my short research project for the ITB-Zernike Master Sandwich program, I was eager/delighted to join your group and continue the work on enzymatic polymerization. Thank you for the effort and support you provided during the proposal preparation, which made it possible for me to obtain a scholarship from LPDP to undertake my PhD. I also want to thank you for entrusting me with the freedom to develop my own ideas and use my creativity in this research project. I appreciate all the valuable experiences that I gained in your research group and I am sincerely grateful for your kindness and help throughout my study. Thank you so much for your understanding to give me an extended leave of absence when I needed it, my family and I greatly appreciate it. Vielen Dank.

I sincerely thank my co-promotor Prof. Cynthia L. Radiman. Ibu Cynthia, I have learned so many great things from you and I always respect you. Thank you for all help and guidance throughout my bachelor, master and now PhD program. Thank you very much for your word of inspiration and encouragement to pursue higher education and for me to be a better person. Terima kasih banyak Bu saya sudah diantar sampai dapat gelar doktor. Semoga Tuhan YME senantiasa membalas kebaikan Ibu. I would like to thank the members of the assessment committee: Prof. Francesco Picchioni from the University of Groningen, Prof. Frank Hollmann from Delft University of Technology, and Prof.

Alessandro Gandini from the University of São Paulo, for their valuable time and effort to evaluate this thesis.

I gratefully acknowledge the scholarship received to undertake my PhD from Indonesian Endowment Fund for Education (Lembaga Pengelola Dana Pendidikan), Ministry of Finance of Republic of Indonesia.

During my PhD, I had the chance to interact and collaborate with a number of people. I want to thank Dr. Jiang; Yi, I want to thank you for your guidance and share of knowledge about this research. Thank you for helping me at the beginning of my PhD studies. I have learnt a lot from you and I really enjoyed our discussion and collaboration. Your significant contribution in this project is certainly appreciated. I always admire your determination and perseverance, very inspiring, it was a great pleasure to work with you, 謝謝. Dr. Fodor and Dr. Skoczinski, our former group members and my lab mates. Csaba, thank you for all the discussions we had and for helping me in daily basis. Especially in the beginning of my PhD, you helped me a lot with improving my skills to work in the lab. Your scientific and technical skills are incredible and I learned a lot from you. Pia, unexpectedly we have co-authored a couple of publications, thank you for our interesting discussions and collaboration. Thanks to you, now I can see enzyme in a broader point of view. Ich habbe einen schlüssel im schussel! Danke schön! Albert Woortman, Jur van Dijken and Gert Alberda van Ekenstein, talented technicians in our group. Dear Albert, I am sincerely grateful for your support in a number of ways. Your expertise and knowledge of SEC measurement undoubtedly helpful for the completion of this thesis. Thank you very much for helping me with the proof-reading of manuscripts and also translating my summary to Dutch. You are always willing to help me in any situation and give me words of encouragement, which I appreciate very much. Dank u wel. Gert and Jur, thank you for advice and help with the DSC and TGA measurement.

I had the chance to be the daily supervisor of several talented (under)graduate students. Kathi, Daniel, Indra, Señorita Viviana, and Mónica; thank you very much, it was a great pleasure to work with all of you. Thanks to your efforts, we can have fruitful

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discussion in this thesis and even publish some of the works. I wish you all the best in life! Special thanks to Mónica, thank you for writing my biography for this thesis. I am always impressed by your writing skills.

I would like to thank the current and former members of the Macromolecular Chemistry and New Polymeric Materials Group. I would like to thank Karin Woudstra; Karin thank you for all your help with most of administrative work. Thanks to the support and good spirit that you’re spreading, I had a nice, gezellig moments and always feel safe in the group. Dr. Erythrina Stavila and Dr. Azis Adharis; Teh Eryth thank you for helping me for adapting with the group and helping me in the beginning of my master research, hatur nuhun pisan Teh. Ka Azis, thank you for all the advice and conversation related to the research as well as the scholarship matter. Thanks to you being my office mate, I have constant motivation for writing. Hatur nuhun Ka Azis, sukses terus di Indonesia. Dr. Maho Nakajima and Dr. Hajime Nakajima; Maho and Nakajima-san thank you for nice conversation and sharing of knowledge related to this project. All the best for you and your family. 有難うございます. Milad Golkaram; Milad thank you for proofreading some of my writing, all the nice scientific and non-scientific discussion. I am grateful that I can be involved in one of your works. Dr. Niels Meereboer; Niels thank you for your help with some technical stuff in the lab. You’re always helpful if I have any question related to the research, and I really appreciate that. Of course I also enjoy the jokes and conversation we had in the office. Dr. Anton Hofman; Anton you are always helpful with anything, thank you for helping me with proofreading and giving good advice throughout my PhD. Dr. Vincent Voet; Vincent thank you for kindly helping me with the proposal preparation to start my PhD in Katja’s group. You are always helpful to everyone and it is always nice to talk with you. Laura Boetje; Laura thank you for helping me to translate the short abstract to Dutch. To the rest of the people in the polymer chemistry department, thank you for maintaining a pleasant working atmosphere: Prof. Marleen Kamperman, Prof. Andreas Herrmann, Dr. Guiseppe Portale, Dr. Bart Crielaard, Chongnan, Aldo, Jingjin, Qi, Maryam, Marco, Federico, Renato, Yassaroh, Fitri, Crystal, Annemarie, Larissa, Feni, Quiyan, Jin, Abednego, Mora, Nanda, Apostolos, Salomeh, Peter, Myleidi, Katherine, Pascal, Harm, Piet, Dennis, Inge, Dejan,

Clemens, Marjon, Pavlo, Eliza, Karolin, Kseniya, Rahul, Ankush, Yexing and others that cannot all be listed here. Over the past years, I had a great time: nice chat, lunch, dinner and drinks, BBQ, bowling, dances, conferences and group meetings.

To all Indonesians in Groningen, living away from homeland feels easier with the help from the big Indonesian Community: Kak Almas, Kak Fean, Mbak Tiur, Mas Tri, Mas Yoga, Mbak Ira, Mbak Ira Sianturi, Bu Ima, Mbak Nur, Mas Adjie, Mas Ronny, Pak Tjiekok, Mas Riswandy, Mas Ury, Mbak Erna, Aisyah, Caca, Nadya, Mas Udin, Bibit, Teh Intan-Mas Rully, Mbak Nuri-Mas Adhyat, Teh Susan-Kang Bino, Ibu Rini-Pak Asmoro, Teh Monik-Mas Fajar, Mbak Ayu-Mas Zainal, Mbak Rosel-Mas Didik, Mbak Fitri-Mas Kus, Mbak Icha-Mas Krisna, Mbak Putri-Mas Amak, Anis-Didin, Carien-Azkario, Mas Azka Muji, Erlangga, Teh Sofi-Mas Bintoro, Mas Chalis, Guntur, Shiddiq, Mbak Inda, Mbak Frita, Mbak Laksmi-Bli Kadek, Uwak Aisah, Bude Arie-Om Herman, Tante Indah-Om Yon, Bude Nunung, Ka Iqbal, Ka Irfan-Teh Liza Miaw, Teh Astri, Teh Amalina, Teh Yosi-Mas Ali, Mbak Desti-Mas Iging, Mas Radit-Mbak Nia, Mas Surya, Mbak Nuril, Mbak Isni, Mbak Vera, Jessi, Fandi, Mbak Tania, Mbak Adel, Dasha, Hadar, Romel, Ila, Marvel, Frans, Rahma, Vivi, Rendy, Donny, Zaid, Hardian, Mas Jon, Saggaf, Pak Henky, Ka Fikri, Yaya, Teh Fanny, Teh Sofa-Mas Yudi, Mbak Tina-Pak Taufik. Terima kasih kepada seluruh rekan-rekan PPIG dan diaspora yang namanya tidak dapat saya sebutkan satu per satu atas bantuan dan keramahtamahan-nya.

People come and go in life and some of them stay for almost the whole period of my PhD. I am grateful for having them who helped me going through the bittersweet moments and making beautiful memories in the past four years. I would like to thanks my dear friends: Bella, Raissa, Salma, Ruby, Ren, Cella, Cynthia and Vina for talks and supports during my studies. Special thanks to Vina. Vincon¸ makasih ya udah ditemenin keliling-keliling waktu di Sydney. Thanks to Keisia, Sasa, and Ida; three kind hearted and talented young women, for the supports and necessary distraction almost every weekend at the beginning of my stay – Salam mager, salam stagnan~ Member of PL Cetar!: Mei-Ucon, Sugab, Bella, Nabila, Audrey, and Livia, I am happy and grateful for the nice and diverse recreational activity we shared. Ka Reren, thank you for all the help, conversation, and your

(5)

discussion in this thesis and even publish some of the works. I wish you all the best in life! Special thanks to Mónica, thank you for writing my biography for this thesis. I am always impressed by your writing skills.

I would like to thank the current and former members of the Macromolecular Chemistry and New Polymeric Materials Group. I would like to thank Karin Woudstra; Karin thank you for all your help with most of administrative work. Thanks to the support and good spirit that you’re spreading, I had a nice, gezellig moments and always feel safe in the group. Dr. Erythrina Stavila and Dr. Azis Adharis; Teh Eryth thank you for helping me for adapting with the group and helping me in the beginning of my master research, hatur nuhun pisan Teh. Ka Azis, thank you for all the advice and conversation related to the research as well as the scholarship matter. Thanks to you being my office mate, I have constant motivation for writing. Hatur nuhun Ka Azis, sukses terus di Indonesia. Dr. Maho Nakajima and Dr. Hajime Nakajima; Maho and Nakajima-san thank you for nice conversation and sharing of knowledge related to this project. All the best for you and your family. 有難うございます. Milad Golkaram; Milad thank you for proofreading some of my writing, all the nice scientific and non-scientific discussion. I am grateful that I can be involved in one of your works. Dr. Niels Meereboer; Niels thank you for your help with some technical stuff in the lab. You’re always helpful if I have any question related to the research, and I really appreciate that. Of course I also enjoy the jokes and conversation we had in the office. Dr. Anton Hofman; Anton you are always helpful with anything, thank you for helping me with proofreading and giving good advice throughout my PhD. Dr. Vincent Voet; Vincent thank you for kindly helping me with the proposal preparation to start my PhD in Katja’s group. You are always helpful to everyone and it is always nice to talk with you. Laura Boetje; Laura thank you for helping me to translate the short abstract to Dutch. To the rest of the people in the polymer chemistry department, thank you for maintaining a pleasant working atmosphere: Prof. Marleen Kamperman, Prof. Andreas Herrmann, Dr. Guiseppe Portale, Dr. Bart Crielaard, Chongnan, Aldo, Jingjin, Qi, Maryam, Marco, Federico, Renato, Yassaroh, Fitri, Crystal, Annemarie, Larissa, Feni, Quiyan, Jin, Abednego, Mora, Nanda, Apostolos, Salomeh, Peter, Myleidi, Katherine, Pascal, Harm, Piet, Dennis, Inge, Dejan,

Clemens, Marjon, Pavlo, Eliza, Karolin, Kseniya, Rahul, Ankush, Yexing and others that cannot all be listed here. Over the past years, I had a great time: nice chat, lunch, dinner and drinks, BBQ, bowling, dances, conferences and group meetings.

To all Indonesians in Groningen, living away from homeland feels easier with the help from the big Indonesian Community: Kak Almas, Kak Fean, Mbak Tiur, Mas Tri, Mas Yoga, Mbak Ira, Mbak Ira Sianturi, Bu Ima, Mbak Nur, Mas Adjie, Mas Ronny, Pak Tjiekok, Mas Riswandy, Mas Ury, Mbak Erna, Aisyah, Caca, Nadya, Mas Udin, Bibit, Teh Intan-Mas Rully, Mbak Nuri-Mas Adhyat, Teh Susan-Kang Bino, Ibu Rini-Pak Asmoro, Teh Monik-Mas Fajar, Mbak Ayu-Mas Zainal, Mbak Rosel-Mas Didik, Mbak Fitri-Mas Kus, Mbak Icha-Mas Krisna, Mbak Putri-Mas Amak, Anis-Didin, Carien-Azkario, Mas Azka Muji, Erlangga, Teh Sofi-Mas Bintoro, Mas Chalis, Guntur, Shiddiq, Mbak Inda, Mbak Frita, Mbak Laksmi-Bli Kadek, Uwak Aisah, Bude Arie-Om Herman, Tante Indah-Om Yon, Bude Nunung, Ka Iqbal, Ka Irfan-Teh Liza Miaw, Teh Astri, Teh Amalina, Teh Yosi-Mas Ali, Mbak Desti-Mas Iging, Mas Radit-Mbak Nia, Mas Surya, Mbak Nuril, Mbak Isni, Mbak Vera, Jessi, Fandi, Mbak Tania, Mbak Adel, Dasha, Hadar, Romel, Ila, Marvel, Frans, Rahma, Vivi, Rendy, Donny, Zaid, Hardian, Mas Jon, Saggaf, Pak Henky, Ka Fikri, Yaya, Teh Fanny, Teh Sofa-Mas Yudi, Mbak Tina-Pak Taufik. Terima kasih kepada seluruh rekan-rekan PPIG dan diaspora yang namanya tidak dapat saya sebutkan satu per satu atas bantuan dan keramahtamahan-nya.

People come and go in life and some of them stay for almost the whole period of my PhD. I am grateful for having them who helped me going through the bittersweet moments and making beautiful memories in the past four years. I would like to thanks my dear friends: Bella, Raissa, Salma, Ruby, Ren, Cella, Cynthia and Vina for talks and supports during my studies. Special thanks to Vina. Vincon¸ makasih ya udah ditemenin keliling-keliling waktu di Sydney. Thanks to Keisia, Sasa, and Ida; three kind hearted and talented young women, for the supports and necessary distraction almost every weekend at the beginning of my stay – Salam mager, salam stagnan~ Member of PL Cetar!: Mei-Ucon, Sugab, Bella, Nabila, Audrey, and Livia, I am happy and grateful for the nice and diverse recreational activity we shared. Ka Reren, thank you for all the help, conversation, and your

(6)

unconditional support. Thanks to you, my master to PhD living transition in Groningen was so much easier. Ivan Terzić, thank you for your help with a lot of things. Ivan, thanks for proofreading the Chapter 1 of this thesis and for never hesitating to share your scientific insight, I really appreciate it. You can be so serious about works, but to be honest you are a fun person to do crazy stuff with - Hvala! Ik wil graag Martijn Tichelaar bedanken. Martijn; to begin with, thank you for your help with the Dutch translation of this thesis summary. I am also grateful for the time and memories we shared together. Thank you for your kindness, support, and understanding – Bedankt voor alles meneer. I am very grateful to Ka Ali, Ka Liany, and little cici Naureen, thank you for always being very welcoming whenever I come by your house. Thank you for kind (almost every day) invitation to have dinner at your place – Makasih banyak ya Ka, maaf suka ngerepotin terus. To Drie Gezusters and Drie Gezusters 2.0: Caecil, dr. Salva, Masyitha. I always enjoy all the fun things we do – lots of travelling and fun together. Caecilia, thank you for being a good friend and travel buddy. Your help with the proofreading is also really appreciated. Despite of your young age, you are undoubtedly one of those people whom I can depend on, and I am really thankful for that. Makasih banyak ya Cecil. dr. Salva Yurista; Bapak Salva thanks for always reminding me to have some holiday to new and different places. I enjoyed travelling with you because it always involves a lot of rest and relaxing, which I need a lot. Also thank you for always being helpful and supportive. Thanks to you, I learned that it is also important to sometimes enjoy life and have fun. Bedankt Pak! Untuk teman seperjuangan, May, makasih banyak buat semua bantuan dan dukungannya. Thank you for being my paranymph, and being a good friend to share a lot of stories and memories. Semoga dilancarkan segala rencana kedepannya. Thanks to Judith Schöbel; my second paranymph, “daily supervisor”, and an amazing friend. Judith, I have no better words than thank you to relay my gratitude for you. Your help with proofreading and giving constructive comments to almost half of this thesis is really appreciated. All other things that you do for me will not go unnoticed. I enjoy the conversation we had about almost any topic (including topics categorized as off limits in Indonesian culture ☺), jokes, the ‘deal’ that we had, and occasional social times outside the lab. Thanks for being my dinkelchen dealer and

providing me constant supply of chocolate in the office. I am sincerely grateful for your help and support for a lot of things. All the best, and perhaps one day, I will get privilege to meet and work together again with you.

Thanks, most of all, to my beloved family in Indonesia: parents, sisters, brother, and my not so little anymore nephew. I am blessed to have you all, thanks for always be there and for the supports and love you provide throughout my entire life. Jazakumullahu khairan. Alhamdulillah udah beres S3-nya, hatur nuhun nya buat semua doa dan dukungannya. Makasih untuk perhatian dan pengertian-nya. Maaf nya belum bisa bantu banyak, sama suka bawa kapusing pas pulang ke Indonesia. Semoga kita semuanya dikuatkan dan diberikan jalan terbaik sama Allah. Finally, I would like to thank the reader and all the party that has helped in finishing this thesis that I cannot mention here.

Groningen, September 2019 Dina Maniar

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unconditional support. Thanks to you, my master to PhD living transition in Groningen was so much easier. Ivan Terzić, thank you for your help with a lot of things. Ivan, thanks for proofreading the Chapter 1 of this thesis and for never hesitating to share your scientific insight, I really appreciate it. You can be so serious about works, but to be honest you are a fun person to do crazy stuff with - Hvala! Ik wil graag Martijn Tichelaar bedanken. Martijn; to begin with, thank you for your help with the Dutch translation of this thesis summary. I am also grateful for the time and memories we shared together. Thank you for your kindness, support, and understanding – Bedankt voor alles meneer. I am very grateful to Ka Ali, Ka Liany, and little cici Naureen, thank you for always being very welcoming whenever I come by your house. Thank you for kind (almost every day) invitation to have dinner at your place – Makasih banyak ya Ka, maaf suka ngerepotin terus. To Drie Gezusters and Drie Gezusters 2.0: Caecil, dr. Salva, Masyitha. I always enjoy all the fun things we do – lots of travelling and fun together. Caecilia, thank you for being a good friend and travel buddy. Your help with the proofreading is also really appreciated. Despite of your young age, you are undoubtedly one of those people whom I can depend on, and I am really thankful for that. Makasih banyak ya Cecil. dr. Salva Yurista; Bapak Salva thanks for always reminding me to have some holiday to new and different places. I enjoyed travelling with you because it always involves a lot of rest and relaxing, which I need a lot. Also thank you for always being helpful and supportive. Thanks to you, I learned that it is also important to sometimes enjoy life and have fun. Bedankt Pak! Untuk teman seperjuangan, May, makasih banyak buat semua bantuan dan dukungannya. Thank you for being my paranymph, and being a good friend to share a lot of stories and memories. Semoga dilancarkan segala rencana kedepannya. Thanks to Judith Schöbel; my second paranymph, “daily supervisor”, and an amazing friend. Judith, I have no better words than thank you to relay my gratitude for you. Your help with proofreading and giving constructive comments to almost half of this thesis is really appreciated. All other things that you do for me will not go unnoticed. I enjoy the conversation we had about almost any topic (including topics categorized as off limits in Indonesian culture ☺), jokes, the ‘deal’ that we had, and occasional social times outside the lab. Thanks for being my dinkelchen dealer and

providing me constant supply of chocolate in the office. I am sincerely grateful for your help and support for a lot of things. All the best, and perhaps one day, I will get privilege to meet and work together again with you.

Thanks, most of all, to my beloved family in Indonesia: parents, sisters, brother, and my not so little anymore nephew. I am blessed to have you all, thanks for always be there and for the supports and love you provide throughout my entire life. Jazakumullahu khairan. Alhamdulillah udah beres S3-nya, hatur nuhun nya buat semua doa dan dukungannya. Makasih untuk perhatian dan pengertian-nya. Maaf nya belum bisa bantu banyak, sama suka bawa kapusing pas pulang ke Indonesia. Semoga kita semuanya dikuatkan dan diberikan jalan terbaik sama Allah. Finally, I would like to thank the reader and all the party that has helped in finishing this thesis that I cannot mention here.

Groningen, September 2019 Dina Maniar

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