Abstract
The use of conducting polymers in devices makes them desirable due to their allowance for the fabrication of flexible, lightweight, and potentially inexpensive devices. This review explores the synthetic strategies and characterizations of 3,6-substituted carbazole-based polymers, emphasizing the influence of these modifications on their electronic structure and absorption properties. Polymers containing carbazole substituents are widely studied due to their unique optical and electronic properties, high electron-donating ability, and photoconductivity. The structural adaptability of the carbazole with the 3,6-substitution makes it as an outstanding candidate for their integration into polymers and also possesses improved stability and triplet energy. The role of intramolecular charge transfer (ICT) was highlighted by donor–acceptor architectures with tailoring energy levels to extract their advantageous physicochemical characteristics and optimized performances. Collectively, this comprehensive review delves into the burgeoning field of 3,6-substituted carbazole-based polymers and their crucial role in advancing optoelectronic applications. By amalgamating materials design, synthetic strategies, and application-driven insights, the review serves as a valuable resource for researchers to understand the structure–property relationships and foster innovative solutions for next-generation opto-electronic applications.
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Data Availability
Raw data that support the findings are available from the corresponding author, upon reasonable request.
References
Yu JC, Jang JI, Lee BR, Lee G-W, Han JT, Song MH (2014) Highly efficient polymer-based optoelectronic devices using PEDOT:PSS and a GO composite layer as a hole transport layer. ACS Appl Mater Interfaces 6(3):2067–2073
Higginbotham H, Karon K, Ledwon P, Data P (2017) Carbazoles in optoelectronic applications. Disp Imaging 2(3–4):207–216
Hfaiedh A, Labiedh M, Mabrouk A, Braiek MB, Alimi K (2023) Synthesis, characterization and structure–property study of new push–pull carbazole materials. Macromol Res 31(10):981–999
Li X, Liu Z, Li C, Gao R, Qi Y, Ren Y (2023) Synthesis and photophysical properties of carbazole-functionalized diazaphosphepines via sequent P-N chemistry. J Org Chem 88(19):13678–13685
Zhang K, Wang X, Chang Y, Wu Y, Wang S, Wang LJ (2023) Carbazole‐decorated organoboron emitters with low‐lying HOMO levels for solution‐processed narrowband blue hyperfluorescence OLED devices. Angew Chem e202313084
Grigoras M, Antonoaia N-C (2005) Synthesis and characterization of some carbazole-based imine polymers. Eur Polym J 41(5):1079–1089
Guo L, Deng J, Zhang L, Xiu Q, Wen G, Zhong C (2012) Synthesis and applications of 3,6-carbazole-based conjugated side-chain copolymers containing complexes of 1,10-phenanthroline with Zn(II), Cd(II) and Ni(II) for dye-sensitized solar cells. Dyes Pigm 92(3):1062–1068
Liu J, Hou W, Xu R, Gao Y, Xu L, Jiang L, Zhang C (2022) Synthesis and electrochemical properties of donor–acceptor-conjugated polymers based on carbazole-EDOT derivatives with different electron-withdrawing groups. ACS Appl Polym Mater 4(3):2132–2139
Radhakrishna K, Manjunath SB, Devadiga D, Chetri R, Nagaraja AT (2023) Review on carbazole-based hole transporting materials for perovskite solar cell. ACS Appl Energy Mater 6(7):3635–3664
Luizys P, Xia J, Daskeviciene M, Kantminiene K, Kasparavicius E, Kanda H, Zhang Y, Jankauskas V, Rakstys K, Getautis V, Nazeeruddin MK (2021) branched methoxydiphenylamine-substituted carbazole derivatives for efficient perovskite solar cells: bigger is not always better. Chem Mater 33(17):7017–7027
Kulasi A, Yi H, Iraqi A (2007) Triarylamine N-functionalized 3,6-linked carbazole main chain polymers and copolymers: Preparation and physical properties. J Polym Sci, Part A: Polym Chem 45(24):5957–5967
Lai M-H, Tsai J-H, Chueh C-C, Wang C-F, Chen W-C (2010) Syntheses of new 3,6-carbazole-based donor/acceptor conjugated copolymers for optoelectronic device applications. Macromol Chem Phys 211(18):2017–2025
Fei T, Cheng G, Hu D, Lu P, Ma Y (2009) A wide band gap polymer derived from 3,6-carbazole and tetraphenylsilane as host for green and blue phosphorescent complexes. J Polym Sci, Part A: Polym Chem 47(18):4784–4792
Sathiyan G, Thangamuthu R, Sakthivel P (2016) Synthesis of carbazole-based copolymers containing carbazole-thiazolo[5,4-d]thiazole groups with different dopants and their fluorescence and electrical conductivity applications. RSC Adv 6(73):69196–69205
Keremane KS, Adhikari AV (2021) Simple carbazole derivatives with mono/dimethoxyphenylacrylonitrile substituents as hole-transporting materials: Performance studies in hybrid perovskite solar cells. Electrochem Sci Adv 1(3):e2000036
Sanda F, Kawasaki R, Shiotsuki M, Takashima T, Fujii A, Ozaki M, Masuda T (2007) Synthesis and properties of polyacetylenes connecting carbazole at the 2- and 3-positions: effect of polymerization catalysts and substitution positions on the optoelectronic properties. Macromol Chem Phys 208(7):765–771
Jenekhe SA, Lu L, Alam MM (2001) New conjugated polymers with donor−acceptor architectures: synthesis and photophysics of carbazole−quinoline and phenothiazine−quinoline copolymers and oligomers exhibiting large intramolecular charge transfer. Macromolecules 34(21):7315–7324
Hu L, Liao G, Guo T, Gao H, Ying L, Cao Y (2019) Wide bandgap poly(meta-styrene) derivatives containing pendant carbazolyl groups as hosts for efficient solution-processed organic light emitting diodes. Polym Chem 10(32):4449–4458
Xu F, Kim J-H, Kim HU, Jang J-H, Yook KS, Lee JY, Hwang D-H (2014) Synthesis of high-triplet-energy host polymer for blue and white electrophosphorescent light-emitting diodes. Macromolecules 47(21):7397–7406
Wang H, Ryu J-T, Kim DU, Han YS, Park LS, Cho H-Y, Lee S-J, Kwon Y (2007) Green and red electrophosphorescent devices consisting of cabazole/triarylamine-based polymers doped with iridium complexes. Mol Cryst Liq Cryst 471(1):279–291
Zhang K, Tao Y, Yang C, You H, Zou Y, Qin J, Ma D (2008) Synthesis and properties of carbazole main chain copolymers with oxadiazole pendant toward bipolar polymer host: Tuning the HOMO/LUMO level and triplet energy. Chem Mater 20(23):7324–7331
Chen B, Yu L, Liu B, Feng J, Liu Z, Ying L, Li Y, Yang W (2014) Efficient π-conjugated interrupted host polymer by metal-free polymerization for blue/green phosphorescent light-emitting diodes. J Polym Sci, Part A: Polym Chem 52(7):1037–1046
Zhang K, Chen Z, Yang C, Gong S, Qin J, Cao Y (2006) Saturated red-emitting electrophosphorescent polymers with iridium coordinating to β-diketonate units in the main chain. Macromol Rapid Commun 27(22):1926–1931
Ying L, Zou J, Zhang A, Chen B, Yang W, Cao Y (2009) Novel orange-red light-emitting polymers with cyclometaled iridium complex grafted in alkyl chain. J Organomet Chem 694(17):2727–2734
Zhen H, Luo J, Yang W, Chen Q, Ying L, Jianhua Z, Wu H, Cao Y (2007) Novel light-emitting electrophosphorescent copolymers based on carbazole with an Ir complex on the backbone. J Mater Chem 17(27):2824–2831
Fei T, Cheng G, Hu D, Dong W, Lu P, Ma Y (2010) Iridium complex grafted to 3,6-carbazole-alt-tetraphenylsilane copolymers for blue electrophosphorescence. J Polym Sci, Part A: Polym Chem 48(9):1859–1865
Chen F, Liu Y, Pan J, Zhu A, Bao J, Yue X, Li Z, Wang S, Ban X (2020) Carbazole-modified polyphenylene ether as host materials for high efficiency phosphorescent organic light-emitting diodes. Opt Mater 101
Huang J, Niu Y, Yang W, Mo Y, Yuan M, Cao Y (2002) Novel electroluminescent polymers derived from carbazole and benzothiadiazole. Macromolecules 35(16):6080–6082
Balaji G, Shim WL, Parameswaran M, Valiyaveettil S (2009) Thiadiazole Fused Indolo[2,3-a]carbazole Based Oligomers and Polymer. Org Lett 11(19):4450–4453
Wang R, Wang W-Z, Yang G-Z, Liu T, Yu J, Jiang Y (2008) Synthesis and characterization of highly stable blue-light-emitting hyperbranched conjugated polymers. J Polym Sci, Part A: Polym Chem 46(3):790–802
Lei Y, Niu Q, Mi H, Wang Y, Nurulla I, Shi W (2013) Carbazole-based conjugated polymer with tethered acetylene groups: Synthesis and characterization. Dyes Pigm 96(1):138–147
Sun D, Fu Q, Ren Z, Li W, Li H, Ma D, Yan S (2013) Carbazole-based polysiloxane hosts for highly efficient solution-processed blue electrophosphorescent devices. J Mater Chem C 1(34):5344–5350
Zhang B, Li B, Wang Z (2020) Creation of carbazole-based fluorescent porous polymers for recognition and detection of various pesticides in water. ACS Sens 5(1):162–170
Qu J, Shiotsuki M, Kobayashi N, Sanda F, Masuda T (2007) Synthesis and properties of carbazole-based hyperbranched conjugated polymers. Polymer 48(22):6481–6490
Wang Y, Zhu Y, Lin X, Yang Y, Zhang B, Zhan H, Xie Z, Cheng Y (2018) Efficient non-doped yellow OLEDs based on thermally activated delayed fluorescence conjugated polymers with an acridine/carbazole donor backbone and triphenyltriazine acceptor pendant. J Mater Chem C 6(3):568–574
Kocaeren AA (2015) Electrochemical synthesis and electrochromic application of a novel polymer based on carbazole. Org Electron 24:219–226
Devadiga D, Selvakumar M, Shetty P, Santosh MS (2021) Recent progress in dye sensitized solar cell materials and photo-supercapacitors: A review. J Power Sources 493:229698
Devadiga D, Selvakumar M, Shetty P, Santosh MS (2021) Dye-sensitized solar cell for indoor applications: A mini-review. J Electron Mater 50(6):3187–3206
Devadiga D, Selvakumar M, Shetty P, Sridhar Santosh M, Chandrabose RS, Karazhanov S (2021) Recent developments in metal-free organic sensitizers derived from carbazole, triphenylamine, and phenothiazine for dye-sensitized solar cells. Int J Energy Res 45(5):6584–6643
Devadiga D, Selvakumar M, Shetty P, Santosh MS (2022) The integration of flexible dye-sensitized solar cells and storage devices towards wearable self-charging power systems: A review. Renew Sustain Energy Rev 159
Sathiyan G, Sivakumar EKT, Ganesamoorthy R, Thangamuthu R, Sakthivel P (2016) Review of carbazole based conjugated molecules for highly efficient organic solar cell application. Tetrahedron Lett 57(3):243–252
Lee JF, Hsu SLC, Lee PI, Chuang HY, Yang ML, Chen JS, Chou WY (2011) Low bandgap carbazole copolymers containing an electron-withdrawing side chain for solar cell applications. Sol Energy Mater Sol Cells 95(10):2795–2804
Zhou J, Yu X, Jin X, Tang G, Zhang W, Hu J, Zhong C (2014) Novel carbazole-based main chain polymeric metal complexes containing complexes of phenanthroline with Zn(II) or Cd(II): Synthesis, characterization and photovoltaic application in DSSCs. J Mol Struct 1058:14–21
Chan L-H, Lin L-C, Yao C-H, Liu Y-R, Jiang Z-J, Cho T-Y (2013) Synthesis of indolo[3,2-b]carbazole-based random copolymers for polymer solar cell applications. Thin Solid Films 544:386–391
Mansha M, Khan I, Ullah N, Qurashi A (2017) Synthesis, characterization and visible-light-driven photoelectrochemical hydrogen evolution reaction of carbazole-containing conjugated polymers. Int J Hydrogen Energy 42(16):10952–10961
Souharce B, Kudla CJ, Forster M, Steiger J, Anselmann R, Thiem H, Scherf U (2009) Amorphous Carbazole-based (Co)polymers for OFET Application. Macromol Rapid Commun 30(14):1258–1262
Xiao H, Xie D, Xue Y (2002) Density functional theory studies on the structures and vibrational spectra of 3,6-dichlorocarbazole and 3,6-dibromocarbazole. Spectrochim Acta Part A Mol Biomol Spectrosc 58(10):2227–2235
Lee SY, Boo BH (1996) Molecular structures and vibrational spectra of pyrrole and carbazole by density functional theory and conventional ab initio calculations. J Phys Chem 100(37):15073–15078
Konidena RK, Thomas KRJ, Park JW (2022) recent advances in the design of multi-substituted carbazoles for optoelectronics: Synthesis and structure-property outlook. ChemPhotoChem 6(10):e202200059
Funding
JAIN (Deemed-to-be University), Bangalore, Karnataka, India under Minor Project Grant, JU/MRP/CNMS/14/2022, Science and Engineering Research Board (SERB), Govt. of India, New Delhi, India under Core Research Grant, CRG/2020/003151.
Author information
Authors and Affiliations
Contributions
Srikanth G: Conceptualization, Methodology, Software, Writing – original draft. Deepak Devadiga: Conceptualization, Software, Writing – review & editing. Samrudhi BM: Software, Writing – review & editing. T.N. Ahipa: Supervision, Writing – review & editing, funding acquisition.
Corresponding author
Ethics declarations
Ethical Approval
Not applicable.
Conflict of Interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
G., S., Devadiga, D., B. M., S. et al. Synthetic Strategies for 3,6-Substituted Carbazole-based Polymers and Their Opto-Electronic Applications—A Review. J Fluoresc (2024). https://doi.org/10.1007/s10895-023-03535-2
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10895-023-03535-2