Functional Block Copolymers Carrying One Double-Stranded Ladderphane and One Single-Stranded Block in a Facile Metathesis Cyclopolymerization Procedure
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. Synthesis of Didodecydipropargylmalonate (DDDPM)
3.2. Block Copolymerization
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
PDI | Perylene diimide |
MCP | Metathesis cyclopolymerization |
Ru-III | Grubbs third-generation catalyst |
GPC | Gel Permeation Chromatography |
CV | Cyclic voltammetry |
TGA | Thermogravimetric analysis |
LUMO | Lower unoccupied molecular orbital |
DDDPM | Dipropargylmalonate |
EDCI·HCl | 1-(3-dimethylaminoprop-yl)-3-ethylcarbodiimidehydrochloride |
DMAP | 4-dimethylaminopyridine |
GPC | Gel permeation chromatography |
PCBM | [6,6]-phenyl-C61-butyric acid methyl ester |
References
- Yang, J.; Yin, Y.L.; Chen, F.; Zhang, Y.; Xiao, B.; Zhao, L.C.; Zhou, E.J. Comparison of three n-type copolymers based on benzodithiophene and naphthalene diimide/perylene diimide/fused perylene diimides for all-polymer solar cells application. ACS Appl. Mater. Interfaces 2018, 10, 23263–23269. [Google Scholar] [CrossRef] [PubMed]
- Ma, L.C.; Qin, D.S.; Liu, Y.Q.; Zhan, X.W. N-Type organic light-emitting transistors with high mobility and improved air stability. J. Mater. Chem. C 2018, 6, 535–540. [Google Scholar] [CrossRef]
- Jia, J.C.; Fan, B.B.; Xiao, M.J.; Jia, T.; Jin, Y.C.; Li, Y.; Huang, F.; Cao, Y. N-Type Self-Doped Water/Alcohol-Soluble Conjugated Polymers with Tailored Energy Levels for High-Performance Polymer Solar Cells. Macromolecules 2018, 51, 2195–2202. [Google Scholar] [CrossRef]
- Zhang, Y.D.; Guo, X.; Su, W.Y.; Guo, B.; Xu, Z.; Zhang, M.J.; Li, Y.F. Perylene diimide-benzodithiophene D-A copolymers as acceptor in all-polymer solar cells. Org. Electron. 2017, 41, 49–55. [Google Scholar] [CrossRef]
- Shi, Y.Q.; Guo, H.; Qin, M.C.; Wang, Y.X.; Zhao, J.Y.; Sun, H.L.; Wang, H.; Wang, Y.L.; Zhou, X.; Facchetti, A.; et al. Imide-Functionalized Thiazole-Based Polymer Semiconductors: Synthesis, Structure-Property Correlations, Charge Carrier Polarity, and Thin-Film Transistor Performance. Chem. Mater. 2018, 30, 7988–8001. [Google Scholar] [CrossRef]
- Zhan, C.L.; Yao, J.N. More than Conformational “Twist” or “Coplanarity”: Molecular Strategies for Designing High-Efficiency Nonfullerence Organic Solar Cells. Chem. Mater. 2016, 28, 1948–1964. [Google Scholar] [CrossRef]
- Ke, Y.Z.; Huang, S.L.; Lai, G.Q.; Luh, T.Y. Selective ring-opening metathesis polymerization (ROMP) of cyclobutenes. Unsymmetricalladderphanecontaining polycyclobutene and polynorbornene strands. Beilstein J. Org. Chem. 2019, 15, 44–51. [Google Scholar] [CrossRef]
- Chen, J.; Li, H.F.; Zhang, H.C.; Liao, X.J.; Han, H.J.; Zhang, L.D.; Sun, R.Y.; Xie, M.R. Blocking-cyclization technique for precise synthesis of cyclic polymers with regulated topology. Nat. Commun. 2018, 9, 1–9. [Google Scholar] [CrossRef] [Green Version]
- Luh, T.Y. Ladderphanes: A New Type of Duplex Polymers. Acc. Chem. Res. 2013, 46, 378–389. [Google Scholar] [CrossRef]
- Ke, Y.Z.; Ji, R.J.; Wei, T.C.; Lee, S.L.; Huang, S.L.; Huang, M.J.; Chen, C.h.; Luh, T.Y. Well-Defined Condensation Polymers with Narrow Polydispersity via Unsymmetrical Ladderphanes by Sequential Polymerization. Macromolecules 2013, 46, 6712–6722. [Google Scholar] [CrossRef]
- Jiang, W.; Xiao, C.; Hao, L.; Wang, Z.; Ceymann, H.; Lambert, C.; Motta, S.D.; Negri, F. Localization/Delocalization of Charges in Bay-Linked Perylene Bisimides. Chem. Eur. J. 2012, 18, 6764–6775. [Google Scholar] [CrossRef] [PubMed]
- Song, W.; Han, H.J.; Wu, J.H.; Xie, M.R. Ladder-like polyacetylene with excellent optoelectronic properties and regular architecture. Chem. Commun. 2014, 50, 12899–12902. [Google Scholar] [CrossRef] [PubMed]
- Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L.D.A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Photo-luminescence and Conductivity of Self-Assembled p-p Stacks of Perylene Bisimide Dyes. Chem. Eur. J. 2007, 13, 436–449. [Google Scholar] [CrossRef] [PubMed]
- Kang, E.H.; Lee, I.S.; Choi, T.L. Ultrafast Cyclopolymerization for Polyene Synthesis: Living Polymerization to Dendronized Polymers. J. Am. Chem. Soc. 2011, 133, 11904–11907. [Google Scholar] [CrossRef] [PubMed]
- Kang, E.H.; Lee, I.H.; Choi, T.L. Brush Polymers Containing Semiconducting Polyene Backbones: Graft-Through Synthesis via Cyclopolymerization and Conformational Analysis on the Coil-to-Rod Transition. ACS Macro Lett. 2012, 1, 1098–1102. [Google Scholar] [CrossRef]
- Motomura, Y.; Hattori, Y.; Sakurai, T.; Ghosh, S.; Seki, S. Impact of Unsymmetrical Alkyl−Fluoroalkyl Side Chains over Coil-to-Rod Transition of Soluble Polyacetylenes: Modulation of Electronic Conjugation of Isolated Chains and Their Self-Assembly. Macromolecules 2019, 52, 4916–4925. [Google Scholar] [CrossRef]
- Li, Y.; Cao, Y.; Gao, J.; Wang, D.; Yu, G.; Heeger, A.J. Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells. Synthetic Met. 1999, 99, 243–248. [Google Scholar] [CrossRef]
- Li, J.; Kastler, M.; Pisula, W.; Robertson, J.W.F.; Wasserfallen, D.; Grimsdale, A.C.; Wu, J.; Mullen, K. Organic Bulk‐Heterojunction Photovoltaics Based on Alkyl Substituted Discotics. Adv. Funct. Mater. 2007, 17, 2528–2533. [Google Scholar] [CrossRef]
- Sullivan, P.; Collis, E.G.; Rochford, L.A.; Arantes, J.F.; Kemppinen, P.; Jones, T.S.; Winzenberg, K.N. An N-ethylated barbituric acid end-capped bithiophene as an electron-acceptor material in fullerene-free organic photovoltaics. Chem. Commun. 2015, 51, 6222–6225. [Google Scholar] [CrossRef]
- Zagranyarski, Y.L.; Chen, L.; Jansch, D.; Gessner, T.; Li, C.; Mullen, K. Toward Perylene Dyes by the Hundsdiecker Reaction. Org. Lett. 2014, 16, 2814–2817. [Google Scholar] [CrossRef]
- Peterson, G.I.; Yang, S.; Choi, T.L. Synthesis of Functional Polyacetylenes via Cyclopolymerization of Diyne Monomers with Grubbs-type Catalysts. Acc. Chem. Res. 2019, 52, 994–1005. [Google Scholar] [CrossRef] [PubMed]
- Song, J.A.; Choi, T.L. Seven-Membered Ring-Forming Cyclopolymerization of 1,8- Nonadiyne Derivatives Using Grubbs Catalysts: Rational Design of Monomers and Insights into the Mechanism for Olefin Metathesis Polymerizations. Macromolecules 2017, 50, 2724–2735. [Google Scholar] [CrossRef]
- Lee, I.S.; Kang, E.H.; Park, H.; Choi, T.L. Controlled cyclopolymerisation of 1,7-octadiyne derivatives using Grubbs catalyst. Chem. Sci. 2012, 3, 761–765. [Google Scholar] [CrossRef]
- Carney, J.M.; Donoghue, P.J.; Wuest, W.M.; Wiest, O.; Helquist, P. Intramolecular Hydroamination of Aminoalkynes with Silver-Phenanthroline Catalysts. Org. Lett. 2008, 10, 3903–3906. [Google Scholar] [CrossRef]
Run | Sample | [M]/[I] a | Mnc (kDa) | PDI d | Yield e (%) | λabsf (nm) | Egg (eV) | LUMO h (eV) |
---|---|---|---|---|---|---|---|---|
1 | Poly(1)-b-Poly(DDDM) | 10:80:1 | 39.5 | 1.3 | 98 | / | / | |
2 | Poly(1)-b-Poly(DDDM) | 20:80:1 | 48.8 | 1.5 | 95 | 800 | 1.55 | −4.3 |
3 | Poly(1)-b-Poly(DDDM) | 40:80:1 | 34.6/72.5 | 1.4/1.5 | 76 | / | / | |
4 | Poly(2)-b-Poly(DDDM) | 20:80:1 | 52.1 | 1.6 | 85 | / | / | |
5 | Poly(2)-b-Poly(DDDM) | 40:80:1 | 66.0 | 1.5 | 70 | 800 | 1.55 | −4.0 |
6 | Poly(2)-b-Poly(DDDM) | 60:80:1 | 40.2/83.4 | 1.5/1.6 | 41 | / | / | / |
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Song, W.; Li, Y.; Liu, X.; Xu, Z.; Wu, J.; Ding, L. Functional Block Copolymers Carrying One Double-Stranded Ladderphane and One Single-Stranded Block in a Facile Metathesis Cyclopolymerization Procedure. Int. J. Mol. Sci. 2019, 20, 5166. https://doi.org/10.3390/ijms20205166
Song W, Li Y, Liu X, Xu Z, Wu J, Ding L. Functional Block Copolymers Carrying One Double-Stranded Ladderphane and One Single-Stranded Block in a Facile Metathesis Cyclopolymerization Procedure. International Journal of Molecular Sciences. 2019; 20(20):5166. https://doi.org/10.3390/ijms20205166
Chicago/Turabian StyleSong, Wei, Yadi Li, Xunhu Liu, Zongyi Xu, Jianhua Wu, and Liang Ding. 2019. "Functional Block Copolymers Carrying One Double-Stranded Ladderphane and One Single-Stranded Block in a Facile Metathesis Cyclopolymerization Procedure" International Journal of Molecular Sciences 20, no. 20: 5166. https://doi.org/10.3390/ijms20205166