Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization
Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a&...
Ausführliche Beschreibung
Autor*in: |
Marco Paolino [verfasserIn] Giorgio Grisci [verfasserIn] Annalisa Reale [verfasserIn] Vincenzo Razzano [verfasserIn] Germano Giuliani [verfasserIn] Alessandro Donati [verfasserIn] Raniero Mendichi [verfasserIn] Daniele Piovani [verfasserIn] Antonella C. Boccia [verfasserIn] Alessandro Grillo [verfasserIn] Gianluca Giorgi [verfasserIn] Andrea Cappelli [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
Erschienen: |
2018 |
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Übergeordnetes Werk: |
In: Polymers - MDPI AG, 2011, 10(2018), 7, p 752 |
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Übergeordnetes Werk: |
volume:10 ; year:2018 ; number:7, p 752 |
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DOI / URN: |
10.3390/polym10070752 |
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Katalog-ID: |
DOAJ00917611X |
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10.3390/polym10070752 doi (DE-627)DOAJ00917611X (DE-599)DOAJ2bd6d03104094a988940d48ab67dd1d6 DE-627 ger DE-627 rakwb eng QD241-441 Marco Paolino verfasserin aut Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. spontaneous polymerization affinity polymerization π-conjugated polymer through-space conjugated polymer polybenzofulvene Organic chemistry Giorgio Grisci verfasserin aut Annalisa Reale verfasserin aut Vincenzo Razzano verfasserin aut Germano Giuliani verfasserin aut Alessandro Donati verfasserin aut Raniero Mendichi verfasserin aut Daniele Piovani verfasserin aut Antonella C. Boccia verfasserin aut Alessandro Grillo verfasserin aut Gianluca Giorgi verfasserin aut Andrea Cappelli verfasserin aut In Polymers MDPI AG, 2011 10(2018), 7, p 752 (DE-627)61409612X (DE-600)2527146-5 20734360 nnns volume:10 year:2018 number:7, p 752 https://doi.org/10.3390/polym10070752 kostenfrei https://doaj.org/article/2bd6d03104094a988940d48ab67dd1d6 kostenfrei http://www.mdpi.com/2073-4360/10/7/752 kostenfrei https://doaj.org/toc/2073-4360 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2119 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2018 7, p 752 |
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10.3390/polym10070752 doi (DE-627)DOAJ00917611X (DE-599)DOAJ2bd6d03104094a988940d48ab67dd1d6 DE-627 ger DE-627 rakwb eng QD241-441 Marco Paolino verfasserin aut Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. spontaneous polymerization affinity polymerization π-conjugated polymer through-space conjugated polymer polybenzofulvene Organic chemistry Giorgio Grisci verfasserin aut Annalisa Reale verfasserin aut Vincenzo Razzano verfasserin aut Germano Giuliani verfasserin aut Alessandro Donati verfasserin aut Raniero Mendichi verfasserin aut Daniele Piovani verfasserin aut Antonella C. Boccia verfasserin aut Alessandro Grillo verfasserin aut Gianluca Giorgi verfasserin aut Andrea Cappelli verfasserin aut In Polymers MDPI AG, 2011 10(2018), 7, p 752 (DE-627)61409612X (DE-600)2527146-5 20734360 nnns volume:10 year:2018 number:7, p 752 https://doi.org/10.3390/polym10070752 kostenfrei https://doaj.org/article/2bd6d03104094a988940d48ab67dd1d6 kostenfrei http://www.mdpi.com/2073-4360/10/7/752 kostenfrei https://doaj.org/toc/2073-4360 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2119 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2018 7, p 752 |
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10.3390/polym10070752 doi (DE-627)DOAJ00917611X (DE-599)DOAJ2bd6d03104094a988940d48ab67dd1d6 DE-627 ger DE-627 rakwb eng QD241-441 Marco Paolino verfasserin aut Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. spontaneous polymerization affinity polymerization π-conjugated polymer through-space conjugated polymer polybenzofulvene Organic chemistry Giorgio Grisci verfasserin aut Annalisa Reale verfasserin aut Vincenzo Razzano verfasserin aut Germano Giuliani verfasserin aut Alessandro Donati verfasserin aut Raniero Mendichi verfasserin aut Daniele Piovani verfasserin aut Antonella C. Boccia verfasserin aut Alessandro Grillo verfasserin aut Gianluca Giorgi verfasserin aut Andrea Cappelli verfasserin aut In Polymers MDPI AG, 2011 10(2018), 7, p 752 (DE-627)61409612X (DE-600)2527146-5 20734360 nnns volume:10 year:2018 number:7, p 752 https://doi.org/10.3390/polym10070752 kostenfrei https://doaj.org/article/2bd6d03104094a988940d48ab67dd1d6 kostenfrei http://www.mdpi.com/2073-4360/10/7/752 kostenfrei https://doaj.org/toc/2073-4360 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2119 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2018 7, p 752 |
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10.3390/polym10070752 doi (DE-627)DOAJ00917611X (DE-599)DOAJ2bd6d03104094a988940d48ab67dd1d6 DE-627 ger DE-627 rakwb eng QD241-441 Marco Paolino verfasserin aut Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. spontaneous polymerization affinity polymerization π-conjugated polymer through-space conjugated polymer polybenzofulvene Organic chemistry Giorgio Grisci verfasserin aut Annalisa Reale verfasserin aut Vincenzo Razzano verfasserin aut Germano Giuliani verfasserin aut Alessandro Donati verfasserin aut Raniero Mendichi verfasserin aut Daniele Piovani verfasserin aut Antonella C. Boccia verfasserin aut Alessandro Grillo verfasserin aut Gianluca Giorgi verfasserin aut Andrea Cappelli verfasserin aut In Polymers MDPI AG, 2011 10(2018), 7, p 752 (DE-627)61409612X (DE-600)2527146-5 20734360 nnns volume:10 year:2018 number:7, p 752 https://doi.org/10.3390/polym10070752 kostenfrei https://doaj.org/article/2bd6d03104094a988940d48ab67dd1d6 kostenfrei http://www.mdpi.com/2073-4360/10/7/752 kostenfrei https://doaj.org/toc/2073-4360 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2119 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2018 7, p 752 |
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10.3390/polym10070752 doi (DE-627)DOAJ00917611X (DE-599)DOAJ2bd6d03104094a988940d48ab67dd1d6 DE-627 ger DE-627 rakwb eng QD241-441 Marco Paolino verfasserin aut Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. spontaneous polymerization affinity polymerization π-conjugated polymer through-space conjugated polymer polybenzofulvene Organic chemistry Giorgio Grisci verfasserin aut Annalisa Reale verfasserin aut Vincenzo Razzano verfasserin aut Germano Giuliani verfasserin aut Alessandro Donati verfasserin aut Raniero Mendichi verfasserin aut Daniele Piovani verfasserin aut Antonella C. Boccia verfasserin aut Alessandro Grillo verfasserin aut Gianluca Giorgi verfasserin aut Andrea Cappelli verfasserin aut In Polymers MDPI AG, 2011 10(2018), 7, p 752 (DE-627)61409612X (DE-600)2527146-5 20734360 nnns volume:10 year:2018 number:7, p 752 https://doi.org/10.3390/polym10070752 kostenfrei https://doaj.org/article/2bd6d03104094a988940d48ab67dd1d6 kostenfrei http://www.mdpi.com/2073-4360/10/7/752 kostenfrei https://doaj.org/toc/2073-4360 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2119 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2018 7, p 752 |
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Marco Paolino Giorgio Grisci Annalisa Reale Vincenzo Razzano Germano Giuliani Alessandro Donati Raniero Mendichi Daniele Piovani Antonella C. Boccia Alessandro Grillo Gianluca Giorgi Andrea Cappelli |
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Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization |
abstract |
Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. |
abstractGer |
Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. |
abstract_unstemmed |
Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a–h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2′-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated. |
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