Các dẫn xuất Difluoroboranyl làm chất khởi xướng quang hợp hiệu quả trong các phản ứng polymer hóa gốc tự do

Polymer Bulletin - Tập 75 - Trang 3267-3281 - 2017
Beata Jędrzejewska1, Borys Ośmiałowski1
1Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Bydgoszcz, Poland

Tóm tắt

Các hệ thống khởi xướng quang dựa trên các dẫn xuất BF2 và muối tetramethylammonium phenyltriethylborate đã được thử nghiệm trong các phản ứng photopolymer hóa thông qua phương pháp photo-DSC. Tốc độ polymer hóa TMPTA tốt và tỷ lệ chuyển đổi monomer cuối cùng đạt được cho hệ thống được thử nghiệm. Ảnh hưởng của loại hợp chất dị vòng đến các tính chất của chúng đã được tiết lộ. Các quá trình trạng thái kích thích, được nghiên cứu bằng photolysis flash nanosecond, nằm trong một quá trình phân rã khởi xướng quang nhanh chóng dẫn đến các loài phản ứng. Một trạng thái triplet được quan sát cho các dẫn xuất đã được nghiên cứu.

Từ khóa

#Dẫn xuất Difluoroboranyl #Chất khởi xướng quang #Polymer hóa gốc tự do #Photo-DSC #Quá trình trạng thái kích thích

Tài liệu tham khảo

Yılmaz H, Küçüköz B, Sevinç G, Tekin S, Yaglioglu HG, Hayvali M, Elmali A (2013) The effect of charge transfer on the ultrafast and two-photon absorption properties of newly synthesized boron–dipyrromethene compounds. Dyes Pigm 99:979–985. doi:10.1016/j.dyepig.2013.07.036 Zakrzewska A, Zaleśny R, Kolehmainen E, Ośmiałowski B, Jędrzejewska B, Ågren H, Pietrzak M (2013) Substituent effects on the photophysical properties of fluorescent 2-benzoylmethylenequinoline difluoroboranes: a combined experimental and quantum chemical study. Dyes Pigm 99:957–965. doi:10.1016/j.dyepig.2013.08.002 Wang D, Fan J, Gao X, Wang B, Sun S, Peng X (2009) Carboxyl BODIPY dyes from bicarboxylic anhydrides: one-pot preparation, spectral properties, photostability, and biolabeling. J Org Chem 74(20):7675–7683. doi:10.1021/jo901149y Fan G, Yang L, Chen Z (2014) Water-soluble BODIPY and aza-BODIPY dyes: synthetic progress and applications. Front Chem Sci Eng 8:405–417. doi:10.1007/s11705-014-1445-7 Jędrzejewska B, Zakrzewska A, Mlostoń G, Budzák Š, Mroczyńska K, Grabarz AM, Kaczorowska MA, Jacquemin D, Ośmiałowski B (2016) Synthesis and photophysical properties of novel donor–acceptor N-(pyridin-2-yl)-substituted benzo(thio)amides and their difluoroboranyl derivatives. J Phys Chem A 120:4116–4123. doi:10.1021/acs.jpca.6b04004 Papalia T, Siracusano G, Colao I, Barattucci A, Aversa MC, Serroni S, Zappalà G, Campagna S, Sciortino MT, Puntoriero F, Bonaccorsi P (2014) Cell internalization of BODIPY-based fluorescent dyes bearing carbohydrate residues. Dyes Pigm 110:67–71. doi:10.1016/j.dyepig.2014.05.022 Grabarz AM, Laurent AD, Jędrzejewska B, Zakrzewska A, Jacquemin D, Ośmiałowski B (2016) The influence of the π-conjugated spacer on photophysical properties of difluoroboranyls derived from amides carrying a donor group. J Org Chem 81:2280–2292. doi:10.1021/acs.joc.5b02691 Boens N, Leen V, Dehaen W (2012) Fluorescent indicators based on BODIPY. Chem Soc Rev 41(3):1130–1172. doi:10.1039/C1CS15132K Loudet A, Burgess K (2007) BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem Rev 107(11):4891–4932. doi:10.1021/cr078381n Ulrich G, Ziessel R, Harriman A (2008) The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angew Chem Int Ed Engl 47(7):1184–1201. doi:10.1002/anie.200702070 Nepomnyashchii AB, Bard A (2012) Electrochemistry and electrogenerated chemiluminescence of BODIPY dyes. J Acc Chem Res 45(11):1844–1853. doi:10.1021/ar200278b Treibs A, Kreuzer F-H (1968) Difluorboryl-komplexe von di- und tripyrrylmethenen. Justus Liebigs Ann Chem 718(1):208–223. doi:10.1002/jlac19687180119 Xu S, Evans RE, Liu T, Zhang G, Demas JN, Trindle CO, Fraser CL (2013) Aromatic difluoroboron β-diketonate complexes: effects of π-conjugation and media on optical properties. Inorg Chem 52(7):3597–3610. doi:10.1021/ic300077g Matyjaszewski K, Davis TP (2002) Handbook of radical polymerization. Wiley, Hoboken Yagci Y, Jockusch S, Turro JN (2010) Photoinitiated polymerization: advances, challenges, and opportunities. Macromolecules 43:6245–6260. doi:10.1021/ma1007545 Fouassier J-P, Morlet-Savary F, Lalevée J, Allonas X, Ley Ch (2010) Dyes as photoinitiators or photosensitizers of polymerization reactions. Materials 3:5130–5142. doi:10.3390/ma3125130 Fouassier J-P, Allonas X (2010) Basics of photopolymerization reactions. Researchsignpost, Trivandrum Fouassier J-P, Lalevée J (2012) Three-component photoinitiating systems: towards innovative tailor made high performance combinations. RSC Adv 2:2621–2629. doi:10.1039/C2RA00892K Doğruyol Z, Arsu N, Doğruyol SK, Pekcan Ö (2012) Critical phenomenon during photoinitiated gelation at different temperatures: a photo-DSC study. Prog Org Coat 74:181–185. doi:10.1016/j.porgcoat.2011.08.008 Fouassier J-P, Lalevée J (2013) Design of chromophores for photoinitiators of polymerization: brief survey and recent achievements. In: Moliere A, Vigneron E (eds) New developments in chromophore research. Nova Science Publishers, Hauppauge, pp 245–266 Tehfe M-A, El-Roz M, Lalevée J, Morlet-Savary F, Graff B, Fouassier J-P (2012) Bifunctional co-initiators: a new strategy for the design of efficient systems in radical photopolymerization reactions under air. Eur Polym J 48:956–962. doi:10.1016/j.eurpolymj.2012.01.022 Braun D (2009) Origins and development of initiation of free radical polymerization processes. Int J Polym Sci 2009:1–10. doi:10.1155/2009/893234 Xiao P, Zhang J, Dumur F, Tehfe M-A, Morlet-Savary F, Graff B, Gigmes D, Fouassier J-P, Lalevée J (2015) Visible light sensitive photoinitiating systems: recent progress in cationic and radical photopolymerization reactions under soft conditions. Prog Polym Sci 4:32–66. doi:10.1016/j.progpolymsci.2014.09.001 Telitel S, Blanchard N, Schweizer S, Morlet-Savary F, Graff B, Fouassier J-P, Lalevée J (2013) BODIPY derivatives and boranil as new photoinitiating systems of cationic polymerization exhibiting a tunable absorption in the 400–600 nm spectral range. Polymer 54:2071–2076. doi:10.1016/j.polymer.2013.02.013 Telitel S, Lalevée J, Blanchard N, Kavalli T, Tehfe M-A, Schweizer S, Morlet-Savary F, Graff B, Fouassier J-P (2012) Photopolymerization of cationic monomers and acrylate/divinylether blends under visible light using pyrromethene dyes. Macromolecules 45:6864–6868. doi:10.1021/ma301293m Grabarz AM, Zaleśny R, Laurent AD, Jędrzejewska B, Zakrzewska A, Jacquemin D, Ośmiałowski B (2017) The influence of the π-conjugated spacer on photophysical properties of difluoroboranyls derived from amides carrying a donor group. J Org Chem 82:1529–1537. doi:10.1021/acs.joc.5b02691 Zakrzewska A, Kolehmainen E, Valkonen A, Haapaniemi E, Rissanen K, Chęcińska L, Ośmiałowski B (2013) Substituent effect in 2-benzoylmethylenequinoline difluoroborates exhibiting through-space couplings. Multinuclear magnetic resonance, X-ray diffraction, and computational study. J Phys Chem A 117(1):252–256. doi:10.1021/jp311072q Ośmiałowski B, Zakrzewska A, Jędrzejewska B, Grabarz A, Zaleśny R, Bartkowiak W, Kolehmainen E (2015) Influence of substituent and benzoannulation on photophysical properties of 1-benzoylmethyleneisoquinoline difluoroborates. J Org Chem 80:2072–2080. doi:10.1021/jo502244j Pietrzak M, Jędrzejewska B (2011) Synthesis of tetramethylammonium phenyltrialkylborate salts by the addition of alkyllithium reagents to a triorganylborane or organoboranylhalides. J Organomet Chem 696:2135–2141. doi:10.1016/j.jorganchem.2010.11.019 Wu D-E, Lu X-L, Xia M (2015) Study on the solution and solid-state fluorescence of novel BF2 complexes with (Z)-2-[phenanthridin-6(5H)-ylidene]-1-phenylethanone and its derivatives as ligands. New J Chem 39:6465–6473. doi:10.1039/C5NJ00926J Zhang S, Li B, Tang L, Wang X, Liu D, Zhou Q (2001) Studies on the near infrared laser induced photopolymerization employing a cyanine dye–borate complex as the photoinitiator. Polymer 42:7575–7578. doi:10.1016/S0032-3861(01)00233-6 Jędrzejewska B (2013) Factors affecting the TMPTA radical polymerization photoinitiated by phenyltrialkylborates paired with tri-cationic hemicyanine dye. Kinetic studies. Colloid Polym Sci 291(9):2225–2236. doi:10.1007/s00396-013-2964-3 Jędrzejewska B, Pietrzak M (2012) Applicability of hemicyanine phenyltrialkylborate salts as free-radical photoinitiators in the visible-light polymerization of acrylate. J Appl Polym Sci 123:3535–3544. doi:10.1002/app.34865 Tehfe MA, Louradour F, Lalevée J, Fouassier J-P (2013) Photopolymerization reactions: on the way to a green and sustainable chemistry. Appl Sci 3:490–514. doi:10.3390/app3020490 Pączkowski J (2006) Electron-transfer photoinitiators of free radical polymerization. The effect of the co-iniciator structure on photoinitiation ability. In: Fouassier JP (ed) Photochemistry and UV curing: new trends. Research Signpost, Kerala, pp 101–116 Marcus RA (1965) On the theory of electron transfer reactions. VI. Unified treatment for homogeneous and electrode reactions. J Chem Phys 43:679–701. doi:10.1063/1.1696792 Rehm D, Weller A (1970) Kinetics of fluorescence quenching by electron and hydrogen-atom transfer. Isr J Chem 8:259–271. doi:10.1002/ijch.197000029 Keskin S, Jockusch S, Turro NJ, Arsu N (2008) Electron spin resonance and laser flash photolysis study of radical addition to vinyl acrylate and related alkenes. Macromolecules 41:4631–4634. doi:10.1021/jp011813s Zhang J, Campolo D, Dumur F, Xiao P, Fouassier JP, Gigmes D, Lalevée J (2015) Iron complexes as photoinitiators for radical and cationic polymerization through photoredox catalysis processes. J Polym Sci Part A Polym Chem 53:42–49. doi:10.1002/pola.27435 Odian G (1991) Principles of polymerization, 3rd edn. Wiley, New York, p 206 Jiang X, Xu H, Yin J (2004) Polymeric amine bearing side-chain thioxanthone as a novel photoinitiator for photopolymerization. Polymer 45:133–140. doi:10.1016/j.polymer.2003.10.058 Chatterjee S, Davis PD, Gottschalk P, Kurz ME, Sauerwein B, Yang X, Schuster GB (1990) Photochemistry of carbocyanine alkyltriphenylborate salts: intra-ion-pair electron transfer and the chemistry of boranyl radicals. J Am Chem Soc 112(17):6329–6338. doi:10.1021/ja00173a022 Chatterjee S, Gottschalk P, Davis PD, Schuster GB (1988) Electron-transfer reactions in cyanine borate ion pairs: photopolymerization initiators sensitive to visible light. J Am Chem Soc 110:2326–2328. doi:10.1021/ja00215a067 Pozdnyakov IP, Aksenova YuV, Ermolina EG, Melnikov AA, Kuznetsova RT, Grivin VP, Plyusnin VF, Berezin MB, Semeikin AS, Chekalin SV (2013) Photophysics of diiodine-substituted fluorinated boron–dipyrromethene: a time resolved study. Chem Phys Lett 585:49–52. doi:10.1016/j.cplett.2013.08.032 Yang W, Karatay A, Zhao J, Song J, Zhao L, Xing Y, Zhang C, He C, Yaglioglu HG, Hayvali M, Elmali A, Küçüköz B (2015) Near-IR broadband-absorbing trans-bisphosphine Pt(II) bisacetylide complexes: preparation and study of the photophysics. Inorg Chem 54:7492–7505. doi:10.1021/acs.inorgchem.5b01107 Zhang C, Zhao J, Wu S, Wang Z, Wu W, Ma J, Guo S, Huang L (2013) Intramolecular RET enhanced visible light-absorbing Bodipy organic triplet photosensitizers and application in photooxidation and triplet–triplet annihilation upconversion. J Am Chem Soc 135:10566–10578. doi:10.1021/ja405170j Yang P, Zhao J, Wu W, Yu X, Liu Y (2012) Accessing the long-lived triplet excited states in Bodipy-conjugated 2-(2-hydroxyphenyl) benzothiazole/benzoxazoles and applications as organic triplet photosensitizers for photooxidations. J Org Chem 77:6166–6178. doi:10.1021/jo300943t Huang L, Yang W, Zhao J (2014) Switching of the triplet excited state of styryl 2,6-diiodo-Bodipy and its application in acid-activatable singlet oxygen photosensitizing. J Org Chem 79:10240–10255. doi:10.1021/jo5019014 Zhang C, Zhao J, Cui X, Wu X (2015) Thiol-activated triplet–triplet annihilation upconversion: study of the different quenching effect of electron acceptor on the singlet and triplet excited states of Bodipy. J Org Chem 80:5674–5686. doi:10.1021/acs.joc.5b00557 Xu K, Xie Y, Cui X, Zhao J, Glusac KD (2015) DiiodoBodipy–rhodamine dyads: preparation and study of the acid-activatable competing intersystem crossing and energy transfer processes. J Phys Chem B 119:4175–4187. doi:10.1021/jp509858t Wu W, Zhao J, Guo H, Sun J, Ji S, Wang Z (2012) Long-lived room-temperature near-IR phosphorescence of BODIPY in a visible-light-harvesting N^C^N PtII–acetylide complex with a directly metalated BODIPY chromophore. Chem Eur J 18:1961–1968. doi:10.1002/chem.201102634 Huang L, Yu X, Wu W, Zhao J (2012) Styryl Bodipy-C60 dyads as efficient heavy-atom-free organic triplet photosensitizers. Org Lett 14:2594–2597. doi:10.1021/ol3008843 Huang L, Zhao J, Guo S, Zhang C, Ma J (2013) Bodipy derivatives as organic triplet photosensitizers for aerobic photoorganocatalytic oxidative coupling of amines and photooxidation of dihydroxylnaphthalenes. J Org Chem 78:5627–5637. doi:10.1021/jo400769u Fouassier J-P, Allonas X, Burget D (2003) Photopolymerization reactions under visible lights: principle, mechanisms and examples of applications. Prog Org Coat 47:16–36. doi:10.1016/S0300-9440(03)00011-0