Abstract
Phenanthroimidazole-based monomers with reactive vinyl groups were synthesized, and their thermal, optical, photophysical and electrochemical properties were investigated. The monomers exhibited high thermal stability with 5% weight loss temperatures (Td) ranging from 378 to 409 °C. Thermal degradation of the polymerization products apparently takes place in this temperature range. The solutions of the monomers exhibit emission peaks in the range from 388 to 398 nm. In the solid state, the emission of these molecules shows red shift which is coherent with the similar red shifts of the corresponding absorption spectra. Ionization potential values of the compounds estimated by cyclic voltammetry were found to be close and varied in the range from 5.44 to 5.63 eV. Solid-state ionization potentials estimated by photoelectron emission spectrometry varied in the range from 5.54 to 5.66 eV. Self-polymerization of the synthesized monomers was demonstrated by differential scanning calorimetry. The number average molecular weights of the polymerization products of monomers containing substituents at phenyl rings linked to C-2 and N-1 positions of imidazole ring were found to be 100,100 and 196,000, respectively. The apparent activation energy and pre-exponential factor of self-polymerization were found to be dependent on conversion degree. The values of activation energy for self-polymerization of monomers varied in the range from 78.7 to 136.0 kJ/mol (estimated by Ozawa method) and from 78.3 to 139.0 kJ/mol (estimated by Kissinger method).
Similar content being viewed by others
References
Jeon SO, Jang SE, Son HS, Lee JY (2011) External quantum efficiency above 20% in deep blue phosphorescent organic light-emitting diodes. Adv Mater 23:1436–1441. https://doi.org/10.1002/adma.201004372
Wang Z, Lu P, Chen S et al (2011) Phenanthro[9,10-d]imidazole as a new building block for blue emitting materials. J Mater Chem 21:5451–5456. https://doi.org/10.1039/c1Jm10321k
Burroughes JH, Bradley DDC, Brown AR et al (1990) Light-emitting diodes based on conjugated polymers. Nature 347:539–541. https://doi.org/10.1038/347539a0
Bharathan J, Yang Y (1998) Polymer electroluminescent devices processed by inkjet printing: I. Polymer light-emitting logo. Appl Phys Lett 72:2660–2662. https://doi.org/10.1063/1.121090
Zhong C, Duan C, Huang F et al (2011) Materials and devices toward fully solution processable organic light-emitting diodes. Chem Mater 23:326–340. https://doi.org/10.1021/cm101937p
Zuniga CA, Abdallah J, Haske W et al (2013) Crosslinking using rapid thermal processing for the fabrication of efficient solution-processed phosphorescent organic light-emitting diodes. Adv Mater 25:1739–1744. https://doi.org/10.1002/adma.201204518
Zuniga CA, Barlow S, Marder SR (2011) Approaches to solution-processed multilayer organic light-emitting diodes based on cross-linking. Chem Mater 23:658–681. https://doi.org/10.1021/cm102401k
Bacher E, Bayerl M, Rudati P et al (2005) Synthesis and characterization of photo-cross-linkable hole-conducting polymers. Macromolecules 38:1640–1647. https://doi.org/10.1021/ma048365h
Yang X, Müller DC, Neher D, Meerholz K (2006) Highly efficient polymeric electrophosphorescent diodes. Adv Mater 18:948–954. https://doi.org/10.1002/adma.200501867
Zacharias P, Gather MC, Rojahn M et al (2007) New crosslinkable hole conductors for blue-phosphorescent organic light-emitting diodes. Angew Chem Int Ed 46:4388–4392. https://doi.org/10.1002/anie.200605055
Kahle FJ, Saller C, Kohler A, Strohriegl P (2017) Crosslinked semiconductor polymers for photovoltaic applications. Adv Energy Mater 7:1700306. https://doi.org/10.1002/aenm.201700306
Evans TR (1971) Singlet quenching mechanisms. J Am Chem Soc 93:2081–2082. https://doi.org/10.1021/ja00737a058
Wallace WL, Van Duyne RP, Lewis FD (1976) Quenching of aromatic hydrocarbon singlets and aryl ketone triplets by alkyl disulfides. J Am Chem Soc 98:5319–5326. https://doi.org/10.1021/ja00433a044
Klärner G, Lee JI, Lee VY et al (1999) Cross-linkable polymers based on dialkylfluorenes. Chem Mater 11:1800–1805. https://doi.org/10.1021/cm990027l
Ma B, Lauterwasser F, Deng L et al (2007) New thermally cross-linkable polymer and its application as a hole-transporting layer for solution processed multilayer organic light emitting diodes. Chem Mater 19:4827–4832. https://doi.org/10.1021/cm0715500
Liu MS, Yu-Hua N, Ka JW et al (2008) Thermally cross-linkable hole-transporting materials for improving hole injection in multilayer blue-emitting pohosphorescent polymer light-emitting diodes. Macromolecules 41:9570–9580. https://doi.org/10.1021/ma801374w
Cheng YJ, Liao MH, Shih HM et al (2011) Exciplex electroluminescence induced by cross-linked hole-transporting materials for white light polymer light-emitting diodes. Macromolecules 44:5968–5976. https://doi.org/10.1021/ma2006969
Khuong KS, Jones WH, Pryor WA, Houk KN (2005) The mechanism of the self-initiated thermal polymerization of styrene. Theoretical solution of a classic problem. J Am Chem Soc 127:1265–1277. https://doi.org/10.1021/ja0448667
Cheng Y-J, Liu MS, Zhang Y et al (2008) Thermally cross-linkable hole-transporting materials on conducting polymer: synthesis, characterization, and applications for polymer light-emitting devices. Chem Mater 20:413–422. https://doi.org/10.1021/cm071828o
Lin C-Y, Lin Y-C, Hung W-Y et al (2009) A thermally cured 9,9-diarylfluorene-based triaryldiamine polymer displaying high hole mobility and remarkable ambient stability. J Mater Chem 19:3618–3623. https://doi.org/10.1039/b900977a
Ma B, Kim BJ, Poulsen DA et al (2009) Multifunctional crosslinkable iridium complexes as hole transporting/electron blocking and emitting materials for solution-processed multilayer organic light-emitting diodes. Adv Funct Mater 19:1024–1031. https://doi.org/10.1002/adfm.200801071
Zhong C, Liu S, Huang F et al (2011) Highly efficient electron injection from indium tin oxide/cross-linkable amino-functionalized polyfluorene interface in inverted organic light emitting devices. Chem Mater 23:4870–4876. https://doi.org/10.1021/cm2025685
Sun Y, Chien SC, Yip HL et al (2011) Chemically doped and cross-linked hole-transporting materials as an efficient anode buffer layer for polymer solar cells. Chem Mater 23:5006–5015. https://doi.org/10.1021/cm2024235
Wang K, Wang S, Wei J et al (2014) New multifunctional phenanthroimidazole–phosphine oxide hybrids for high-performance red, green and blue electroluminescent devices. J Mater Chem C 2:6817–6826. https://doi.org/10.1039/c4tc00749b
Zhuang S, Shangguan R, Huang H et al (2014) Synthesis, characterization, physical properties, and blue electroluminescent device applications of phenanthroimidazole derivatives containing anthracene or pyrene moiety. Dyes Pigments 101:93–102. https://doi.org/10.1016/j.dyepig.2013.08.027
Wang J, Lin W, Li W (2013) Three-channel fluorescent sensing via organic white light-emitting dyes for detection of hydrogen sulfide in living cells. Biomaterials 34:7429–7436. https://doi.org/10.1016/j.biomaterials.2013.06.013
Ouyang X, Chen D, Zeng S et al (2012) Highly efficient and solution-processed iridium complex for single-layer yellow electrophosphorescent diodes. J Mater Chem 22:23005–23011. https://doi.org/10.1039/c2jm34462a
Jadhav T, Choi JM, Dhokale B, Mobin SM, Lee JY, Misra R (2016) Effect of end groups on mechanochromism and electroluminescence in tetraphenylethylene substituted phenanthroimidazoles. J Phys Chem C 120:18487–18495. https://doi.org/10.1021/acs.jpcc.6b06277
Wang ZM, Song XH, Gao Z et al (2012) Tuning of the electronic and optical properties of 4,4′-bis(1-phenyl-phenanthro[9,10-d]imidazol-2-yl)biphenyl via cyano substitution in un-conjugated phenyl. RSC Adv 2:9635–9642. https://doi.org/10.1039/c2ra21054a
Wang Z, Feng Y, Li H et al (2014) Dimeric phenanthroimidazole for blue electroluminescent materials: the effect of substituted position attached to biphenyl center. Phys Chem Chem Phys 16:10837–10843. https://doi.org/10.1039/c4cp00209a
Gao Z, Liu Y, Wang Z et al (2013) High-efficiency violet-light-emitting materials based on phenanthro[9,10-d]imidazole. Chem Eur J 19:2602–2605. https://doi.org/10.1002/chem.201203335
Yuan Y, Li D, Zhang X et al (2011) Phenanthroimidazole-derivative semiconductors as functional layer in high performance OLEDs. New J Chem 35:1534–1540. https://doi.org/10.1039/c1nj20072k
Huang H, Wang Y, Zhuang S et al (2012) Simple phenanthroimidazole/carbazole hybrid bipolar host materials for highly efficient green and yellow phosphorescent organic light-emitting diodes. J Phys Chem C 116:19458–19466. https://doi.org/10.1021/jp305764b
Yuan Y, Chen JX, Lu F et al (2013) Bipolar phenanthroimidazole derivatives containing bulky polyaromatic hydrocarbons for nondoped blue electroluminescence devices with high efficiency and low efficiency roll-off. Chem Mater 25:4957–4965. https://doi.org/10.1021/cm4030414
Zhang X, Lin J, Ouyang X et al (2013) Novel host materials based on phenanthroimidazole derivatives forhighly efficient green phosphorescent oleds. J Photochem Photobiol A Chem 268:37–43. https://doi.org/10.1016/j.jphotochem.2013.06.012
Chen W-C, Wu G-F, Yuan Y et al (2015) A meta-molecular tailoring strategy towards an efficient violet-blue organic electroluminescent material. RSC Adv 5:18067–18074. https://doi.org/10.1039/c4ra16954a
Xiang J, Cai X, Lou X et al (2015) Biocompatible green and red fluorescent organic dots with remarkably large two-photon action cross sections for targeted cellular imaging and real-time intravital blood vascular visualization. ACS Appl Mater Interfaces 7:14965–14974. https://doi.org/10.1021/acsami.5b03766
Huang H, Wang Y, Wang B et al (2013) Controllably tunable phenanthroimidazole–carbazole hybrid bipolar host materials for efficient green electrophosphorescent devices. J Mater Chem C 1:5899–5908. https://doi.org/10.1039/c3tc30832d
Kong F, Liu Q, Wu X et al (2011) 2-(4-Formylphenyl)phenanthroimidazole as a colorimetric and fluorometric probe for selective fluoride ion sensing. J Fluoresc 21:1331–1335. https://doi.org/10.1007/s10895-011-0858-7
Lin W, Long L, Yuan L et al (2009) A novel ratiometric fluorescent Fe3 + sensor based on a phenanthroimidazole chromophore. Anal Chim Acta 634:262–266. https://doi.org/10.1016/j.aca.2008.12.049
Song KC, Kim H, Lee KM et al (2013) Ratiometric fluorescence sensing of fluoride ions by triarylborane–phenanthroimidazole conjugates. Sens Actuators B Chem 176:850–857. https://doi.org/10.1016/j.snb.2012.09.049
Lee W, Yang Y, Cho N et al (2012) Functionalized organic dyes containing a phenanthroimidazole donor for dye-sensitized solar cell applications. Tetrahedron 68:5590–5598. https://doi.org/10.1016/j.tet.2012.04.074
Noormofidi N, Slugovc C (2007) Acid/base-sensitive ring-opening metathesis polymers based on phenanthroimidazole dyes. Macromol Chem Phys 208:1093–1100. https://doi.org/10.1002/macp.200700038
Shukla T, Arumugaperumal R, Raghunath P et al (2017) Novel supramolecular conjugated polyrotaxane as an acid-basecontrollable optical molecular switch. Sens Actuators B 243:84–95. https://doi.org/10.1016/j.snb.2016.11.130
Gudeika D, Sini G, Jankauskas V et al (2016) Synthesis and properties of the derivatives of triphenylamine and 1,8-naphthalimide with the olefinic linkages between chromophores. RSC Adv 6:2191–2201. https://doi.org/10.1039/C5RA24820E
Gudeika D, Volyniuk D, Grazulevicius JV et al (2016) Derivative of oxygafluorene and di-tert-butyl carbazole as the host with very high hole mobility for high-efficiency blue phosphorescent organic light-emitting diodes. Dyes Pigments 130:298–305. https://doi.org/10.1016/j.dyepig.2016.03.039
Kukhta NA, Volyniuk D, Peciulyte L et al (2015) Structure-property relationships of star-shaped blue-emitting charge-transporting 1,3,5-triphenylbenzene derivatives. Dyes Pigments 117:122–132. https://doi.org/10.1016/j.dyepig.2015.02.013
Lukstaite J, Gudeika D, Grazulevicius JV et al (2010) Copolymers containing electronically isolated indolyl fragments as materials for optoelectronics. React Funct Polym 70:572–577. https://doi.org/10.1016/j.reactfunctpolym.2010.05.001
D’Andrade BW, Datta S, Forrest SR et al (2005) Relationship between the ionization and oxidation potentials of molecular organic semiconductors. Org Electron Phys Mater Appl 6:11–20. https://doi.org/10.1016/j.orgel.2005.01.002
Vasilenko IV, Vaitusionak AA, Sutaite J et al (2017) Simultaneous step-growth and chain-growth cationic polymerization of styrenic monomers bearing carbazolyl groups. Polymer (United Kingdom) 129:83–91. https://doi.org/10.1016/j.polymer.2017.09.036
Ozawa T (1970) Kinetic analysis of derivative curves in thermal analysis. J Therm Anal 2:301–324. https://doi.org/10.1007/bf01911411
Kissinger HE (1957) Reaction kinetics in differential thermal analysis. Anal Chem 29:1702–1706. https://doi.org/10.1021/ac60131a045
Chen CC, Duh YS, Shu CM (2009) Thermal polymerization of uninhibited styrene investigated by using microcalorimetry. J Hazard Mater 163:1385–1390. https://doi.org/10.1016/j.jhazmat.2008.07.151
Boundy RH, Boyer RF (eds) (1952) Styrene, its polymers, copolymers and derivatives (Chapter 7). Reinhold, New York, pp 238–239
Acknowledgements
This research was supported by Research Council of Lithuania (Grant No. TAP LLT-2/2017).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Butkute, R., Peciulyte, L., Lygaitis, R. et al. Phenanthroimidazole-based monomers: synthesis, properties and self-polymerization. Polym. Bull. 76, 153–174 (2019). https://doi.org/10.1007/s00289-018-2373-3
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-018-2373-3