Abstract
Morphological structures with respect to the effect of carbazole derivatization, which are based on conjugated donor–acceptor moieties, are presently explored. In this work, light management studies, organic photovoltaics devices and surface properties are systematically investigated. Two carbazole derivatives Cz–Bt (carbazole–benzothiadiazole) and Cz–Bt–BT (carbazole–benzothiadiazole–bithiophene) are electrosprayed, resulting in triangle and spike (2-D and 3-D pyramids) structures, respectively. These 2-D and 3-D pyramids differ due to an additional bithiophene unit at the molecular level, which has imparted a higher degree of rotational freedom. The effects of derivatives, solution concentrations and solvents vapor pressure on morphology are studied. Further, these submicron-size pyramids are characterized by enhancement in light absorption due to scattering and multi-reflection. It is observed that 2-D pyramids enhance up to 44.4%, whereas 3-D pyramids enhance up to 18.7% of light absorption. Subsequently, these structures are characterized in organic photovoltaics architecture, using various layer design strategies, and, thus, we able to obtain insights about layer addition, with respect to structures size and morphology. In addition, the effect of fabrication procedure assisting in an increase in hydrophobicity is also demonstrated.
Similar content being viewed by others
References
Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868–5923. doi:10.1021/cr900182s
Kim FS, Ren G, Jenekhe SA (2011) One-dimensional nanostructures of π-conjugated molecular systems: assembly, properties, and applications from photovoltaics, sensors, and nanophotonics to nanoelectronics. Chem Mater 23:682–732. doi:10.1021/cm102772x
Shang H, Fan H, Shi Q et al (2010) Solution processable D–A–D molecules based on triphenylamine for efficient organic solar cells. Sol Energy Mater Sol Cells 94:457–464. doi:10.1016/j.solmat.2009.11.005
Tamayo AB, Dang X-D, Walker B et al (2009) A low band gap, solution processable oligothiophene with a dialkylated diketopyrrolopyrrole chromophore for use in bulk heterojunction solar cells. APL Org Electron Photonics 2:73–73. doi:10.1063/1.3086897
Wang T-L, Yeh A-C, Yang C-H et al (2011) Synthesis and photovoltaic properties of a low bandgap donor–acceptor alternating copolymer with benzothiadiazole unit. Sol Energy Mater Sol Cells 95:3295–3302. doi:10.1016/j.solmat.2011.07.021
Jin J-K, Choi J-K, Kim B-J et al (2011) Synthesis and photovoltaic performance of low-bandgap polymers on the basis of 9,9-dialkyl-3,6-dialkyloxysilafluorene. Macromolecules 44:502–511. doi:10.1021/ma102173a
Karpicz R, Puzinas S, Sulskus J et al (2012) Electronic properties of carbazole–fluorene–benzothiadiazole compounds revealed by time resolved spectroscopy and quantum chemistry calculations. Chem Phys 404:82–87. doi:10.1016/j.chemphys.2012.03.007
Xu C, Zhao J, Wang M et al (2013) Electrosynthesis and characterization of a donor–acceptor type electrochromic material from poly(4,7-dicarbazol-9-yl-2,1,3-benzothiadia-zole) and its application in electrochromic devices. Thin Solid Films 527:232–238. doi:10.1016/j.tsf.2012.12.052
Putri SK, Lee MS, Chang DW, Kim JH (2016) Fluorinated benzothiadiazole-based small molecules for photovoltaic applications. Synth Met 220:455–461. doi:10.1016/j.synthmet.2016.07.018
Kuznetsov IE, Susarova DK, Inasaridze LN et al (2015) Synthesis of statistical carbazole–fluorene–thiophene–benzothiadiazole copolymers and their investigation in organic solar cells. Mendeleev Commun 25:277–279. doi:10.1016/j.mencom.2015.07.016
Venkateswararao A, Thomas KRJ, Lee C-P et al (2014) Organic dyes containing carbazole as donor and π-linker: optical, electrochemical, and photovoltaic properties. ACS Appl Mater Interfaces 6:2528–2539. doi:10.1021/am404948w
Thongkasee P, Thangthong A, Janthasing N et al (2014) Carbazole-dendrimer-based donor–π–acceptor type organic dyes for dye-sensitized solar cells: effect of the size of the carbazole dendritic donor. ACS Appl Mater Interfaces 6:8212–8222. doi:10.1021/am500947k
Grova IR, Coutinho DJ, Faria RM, Akcelrud L (2013) Synthesis and photovoltaic performance of a fluorene–bithiophene copolymer. J Polym Res 20:119. doi:10.1007/s10965-013-0119-3
Sathiyan G, Sivakumar EKT, Ganesamoorthy R et al (2016) Review of carbazole based conjugated molecules for highly efficient organic solar cell application. Tetrahedron Lett 57:243–252. doi:10.1016/j.tetlet.2015.12.057
Pisharady SK, Menon CS, Sudarshanakumar C (2005) Optical and electrical properties of carbazole thin film. J Mater Sci 40:2047–2049. doi:10.1007/s10853-005-1230-6
Kato S, Shimizu S, Kobayashi A et al (2014) Systematic structure-property investigations on a series of alternating carbazole–thiophene oligomers. J Org Chem 79:618–629. doi:10.1021/jo402416f
Sahu D, Padhy H, Patra D et al (2010) Synthesis and application of H-bonded cross-linking polymers containing a conjugated pyridyl H-acceptor side-chain polymer and various carbazole-based H-donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells. Polymer 51:6182–6192. doi:10.1016/j.polymer.2010.10.018
Zhao Z, Xu X, Wang H et al (2007) Zigzag molecules from pyrene-modified carbazole oligomers: synthesis, characterization, and application in OLEDs. J Org Chem 73:594–602. doi:10.1021/jo702075r
Wang L, Fu Y, Zhu L et al (2011) Synthesis and photovoltaic properties of low-bandgap polymers based on N-arylcarbazole. Polymer 52:1748–1754. doi:10.1016/j.polymer.2011.02.029
Barpuzary D, Patra AS, Vaghasiya JV et al (2014) Highly efficient one-dimensional ZnO nanowire-based dye-sensitized solar cell using a metal-free, D–π–A-type, carbazole derivative with more than 5% power conversion. ACS Appl Mater Interfaces 6:12629–12639. doi:10.1021/am5026193
Fei-Peng C, Bin X, Zu-Jin Z et al (2010) White organic light-emitting diodes based on electroplex from polyvinyl carbazole and carbazole oligomers blends. Chin Phys B 19:037801. doi:10.1088/1674-1056/19/3/037801
Balaji G, Shim WL, Parameswaran M, Valiyaveettil S (2009) Thiadiazole fused indolo[2,3-a]carbazole based oligomers and polymer. Org Lett 11:4450–4453. doi:10.1021/ol901806q
Chu Z, Wang D, Zhang C et al (2009) Synthesis of dendritic oligo-spiro(fluorene-9,9′-xanthene) derivatives with carbazole and fluorene pendants and their thermal, optical, and electroluminescent properties. Macromol Rapid Commun 30:1745–1750. doi:10.1002/marc.200900268
Tao Y-M, Li H-Y, Xu Q-L et al (2011) Synthesis and characterization of efficient luminescent materials based on 2,1,3-benzothiadiazole with carbazole moieties. Synth Met 161:718–723. doi:10.1016/j.synthmet.2011.01.020
Lee JY, Song KW, Song HJ, Moon DK (2011) Synthesis and photovoltaic property of donor–acceptor type conjugated polymer containing carbazole and 4,7-dithiazolylbenzothiadiazole moiety utilized as a promising electron withdrawing unit. Synth Met 161:2434–2440. doi:10.1016/j.synthmet.2011.09.021
Umeyama T, Watanabe Y, Douvogianni E, Imahori H (2013) Effect of fluorine substitution on photovoltaic properties of benzothiadiazole-carbazole alternating copolymers. J Phys Chem C 117:21148–21157. doi:10.1021/jp407707u
Casey A, Ashraf RS, Fei Z, Heeney M (2014) Thioalkyl-substituted benzothiadiazole acceptors: copolymerization with carbazole affords polymers with large stokes shifts and high solar cell voltages. Macromolecules 47:2279–2288. doi:10.1021/ma5000943
Hu S, Bao X, Liu Z et al (2014) Benzothiadiazole[1,2-b:4,3-b′]dithiophene, a new ladder-type multifused block: synthesis and photovoltaic application. Org Electron 15:3601–3608. doi:10.1016/j.orgel.2014.10.003
Sylvianti N, Kim YW, Marsya MA et al (2016) A–D–A type conjugated oligomers based on benzothiadiazole and their photovoltaic applications. Synth Met 221:127–133. doi:10.1016/j.synthmet.2016.08.012
Ranjith K, Swathi SK, Kumar P, Ramamurthy PC (2010) Pulsed laser deposition film of a donor–acceptor–donor polymer as possible active layer in devices. J Mater Sci 46:2259–2266. doi:10.1007/s10853-010-5065-4
Ranjith K, Swathi SK, Kumar P, Ramamurthy PC (2012) Dithienylcyclopentadienone derivative-co-benzothiadiazole: an alternating copolymer for organic photovoltaics. Sol Energy Mater Sol Cells 98:448–454. doi:10.1016/j.solmat.2011.11.034
Hong M, Ravva MK, Winget P, Brédas J-L (2016) Effect of substituents on the electronic structure and degradation process in carbazole derivatives for blue OLED host materials. Chem Mater 28:5791–5798. doi:10.1021/acs.chemmater.6b02069
Jiang D, Chen S, Xue Z et al (2016) Donor–acceptor molecules based on benzothiadiazole: synthesis, X-ray crystal structures, linear and third-order nonlinear optical properties. Dyes Pigments 125:100–105. doi:10.1016/j.dyepig.2015.10.014
Sakthivel P, Song HS, Chakravarthi N et al (2013) Synthesis and characterization of new indeno[1,2-b]indole-co-benzothiadiazole-based π-conjugated ladder type polymers for bulk heterojunction polymer solar cells. Polymer 54:4883–4893. doi:10.1016/j.polymer.2013.07.004
Zheng J, Zhang H, Zhao Z, Han CC (2012) Construction of hierarchical structures by electrospinning or electrospraying. Polymer 53:546–554. doi:10.1016/j.polymer.2011.12.018
Huang Z-M, Zhang Y-Z, Kotaki M, Ramakrishna S (2003) A review on polymer nanofibers by electrospinning and their applications in nanocomposites. Compos Sci Technol 63:2223–2253. doi:10.1016/S0266-3538(03)00178-7
Park CH, Lee J (2009) Electrosprayed polymer particles: effect of the solvent properties. J Appl Polym Sci 114:430–437. doi:10.1002/app.30498
Scholten E, Dhamankar H, Bromberg L et al (2011) Electrospray as a tool for drug micro- and nanoparticle patterning. Langmuir 27:6683–6688. doi:10.1021/la201065n
Zhang Q, Liu J, Wang X et al (2010) Controlling internal nanostructures of porous microspheres prepared via electrospraying. Colloid Polym Sci 288:1385–1391. doi:10.1007/s00396-010-2273-z
Ramamurthy P, Mishra S et al (2014) Fabrication of hollow microspheres using single step electrospraying process. J Res Updat Polym Sci 3:108–113. doi:10.6000/1929-5995.2014.03.02.5
Wu Y, Clark RL (2007) Controllable porous polymer particles generated by electrospraying. J Colloid Interface Sci 310:529–535. doi:10.1016/j.jcis.2007.02.023
Jung JH, Lee JE, Bae G-N (2013) Use of electrosprayed Sophora flavescens natural-product nanoparticles for antimicrobial air filtration. J Aerosol Sci 57:185–193. doi:10.1016/j.jaerosci.2012.09.004
Kim Y, Lee J, Kang H et al (2012) Controlled electro-spray deposition of highly conductive PEDOT:PSS films. Sol Energy Mater Sol Cells 98:39–45. doi:10.1016/j.solmat.2011.10.025
Chen J-Y, Kuo C-C, Lai C-S et al (2011) Manipulation on the morphology and electrical properties of aligned electrospun nanofibers of poly(3-hexylthiophene) for field-effect transistor applications. Macromolecules 44:2883–2892. doi:10.1021/ma102286m
Wang X, Kim Y-G, Drew C et al (2004) Electrostatic assembly of conjugated polymer thin layers on electrospun nanofibrous membranes for biosensors. Nano Lett 4:331–334. doi:10.1021/nl034885z
Ma M, Gupta M, Li Z et al (2007) Decorated electrospun fibers exhibiting superhydrophobicity. Adv Mater 19:255–259. doi:10.1002/adma.200601449
Khanum KK, K R, Ramamurthy PC (2014) Various architectures of electrosprayed photoactive materials: A step towards light management. In: MRS online proceedings library archive. doi:10.1557/opl.2014.738
Han L, Zu X, Cui Y et al (2014) Novel D–A–π–A carbazole dyes containing benzothiadiazole chromophores for dye-sensitized solar cells. Org Electron 15:1536–1544. doi:10.1016/j.orgel.2014.04.016
Li J, Grimsdale AC (2010) Carbazole-based polymers for organic photovoltaic devices. Chem Soc Rev 39:2399–2410. doi:10.1039/B915995A
Khanum KK, Ramamurthy PC (2015) Design and morphology control of a thiophene derivative through electrospraying using various solvents. RSC Adv 5:60419–60425. doi:10.1039/C5RA06468F
Acknowledgements
The authors would like to acknowledge Dr. Ranjith K. for synthesizing Cz–Bt and Cz–Bt–BT, which was used here as a case study and Gourav Tarafdar for his valuable input in dihedral studies. Further, the authors would like to acknowledge the Department of Science and Technology, India, DST: SR/S3/ME/0051/2012 for financial support.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Khanum, K.K., Ramamurthy, P.C. Effect of molecular architecture on morphology in the nanostructures and its applications in superhydrophobicity and organic photovoltaics. J Mater Sci 53, 1264–1278 (2018). https://doi.org/10.1007/s10853-017-1578-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-017-1578-4