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