Abstract
The design and synthesis of new conjugated luminescent molecules have attracted the attention of researchers because of their various applications, especially in the field of optoelectronic devices. Most of the applications were mainly based on the intramolecular charge transfer (ICT). For this purpose, we designed and synthesized a series of new donor–acceptor based disc type molecules i.e. 2,4,6-tris(4-(alkyloxy)phenyl)pyridines carrying variable alkoxy chains [i.e. n = 2, 4, 6, 8, 10, 12, 14, 16]. Further, the structures of all the synthesized compounds were confirmed by using ATR-IR, 1H-NMR, 13C-NMR, and ESI–MS analysis. Moreover, the photophysical property study indicated that all the molecules are blue light emitting materials, however the change of alkoxy chain length in phenyl arms does not affect their absorption, emission, and energy levels. Besides, the thermal study revealed that core is stable up to 350 °C. Also, the DFT study showed that the photo induced electron transfer caused by HOMO–LUMO excitation in the studied molecules. Therefore, all the molecules have potential applications in optoelectronic applications.
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References
Ashoka AH, Klymchenko AS (2021) Ultrabright fluorescent polymeric nanofibers and coatings based on ionic dye insulation with bulky counterions. ACS Appl Mater Interfaces 13:28889–28898. https://doi.org/10.1021/acsami.1c06436
Crano JC, Flood T, Knowles D et al (1996) Photochromic compounds: Chemistry and application in ophthalmic lenses. Pure Appl Chem 68:1395–1398. https://doi.org/10.1351/pac199668071395
Ali S, Gupta A, Shafiei M, Langford SJ (2021) Recent advances in perylene diimide-based active materials in electrical mode gas sensing. Chemosensors 9:30. https://doi.org/10.3390/chemosensors9020030
Devadiga D, Selvakumar M, Shetty P et al (2021) Novel photosensitizer for dye-sensitized solar cell based on ionic liquid–doped blend polymer electrolyte. J Solid State Electrochem 25:1461–1478. https://doi.org/10.1007/s10008-021-04920-2
Devadiga D, Selvakumar M, Shetty P, Santosh MS (2021) Dye-sensitized solar cell for indoor applications: A mini-review. J Electron Mater 50:3187–3206. https://doi.org/10.1007/s11664-021-08854-3
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. https://doi.org/10.1016/j.jpowsour.2021.229698
Devadiga D, Selvakumar M, Shetty P et al (2021) Recent developments in metal-free organic sensitizers derived from carbazole, triphenylamine, and phenothiazine for dye-sensitized solar cells. Int J Energy Res 45:6584–6643. https://doi.org/10.1002/er.6348
Kunkel C, Margraf JT, Chen K et al (2021) Active discovery of organic semiconductors. Nat Commun 12:1–11. https://doi.org/10.1038/s41467-021-22611-4
Habeeba AU, Saravanan M, Girisun TCS, Anandan S (2021) Nonlinear optical studies of conjugated organic dyes for optical limiting applications. J Mol Struct 1240:130559. https://doi.org/10.1016/j.molstruc.2021.130559
Devadiga D, Ahipa TN (2021) Cyanopyridone doped PMMA films as UV and blue light filters: Preparation and characterization. Optik (Stuttg) 229:166233. https://doi.org/10.1016/j.ijleo.2020.166233
Ahipa TN, Adhikari AV (2014) Trihydrazone functionalized cyanopyridine discoids: Synthesis, mesogenic and optical properties. Tetrahedron Lett 55:495–500. https://doi.org/10.1016/j.tetlet.2013.11.057
Ahipa TN, Kumar V, Adhikari AV (2014) New columnar liquid crystal materials based on luminescent 2-methoxy-3-cyanopyridines. Struct Chem 25:1165–1174. https://doi.org/10.1007/s11224-014-0390-x
Ahipa TN, Kamath PR, Kumar V, Adhikari AV (2014) New luminescent 2-methoxy-6-(4-methoxy-phenyl)-4-p-tolyl-nicotinonitrile: Synthesis, crystal structure, DFT and photophysical studies. Spectrochim Acta - Part A Mol Biomol Spectrosc 124:230–236. https://doi.org/10.1016/j.saa.2014.01.006
Ahipa TN, Adhikari AV (2014) New cyanopyridone based luminescent liquid crystalline materials: Synthesis and characterization. Photochem Photobiol Sci 13:1496–1508. https://doi.org/10.1039/c4pp00031e
Liu Y, Qiu X, Soni S, Chiechi RC (2021) Charge transport through molecular ensembles: Recent progress in molecular electronics. Chem Phys Rev 2:021303. https://doi.org/10.1063/5.0050667
Yarasir MN, Kandaz M, Senkal BF et al (2007) Metal-ion sensing and aggregation studies on reactive phthalocyanines bearing soft-metal receptor moieties; synthesis, spectroscopy and electrochemistry. Polyhedron 26:5235–5242. https://doi.org/10.1016/j.poly.2007.07.042
Penning LC, Dubbelman TM (1994) Fundamentals of photodynamic therapy. Anticancer Drugs 5:139–146. https://doi.org/10.1097/00001813-199404000-00003
Cosa G, Focsaneanu K-S, McLean JRN et al (2001) Photophysical properties of fluorescent DNA-dyes bound to single- and double-stranded DNA in aqueous buffered solution. Photochem Photobiol 73:585–599. https://doi.org/10.1562/0031-8655(2001)073%3c0585:PPOFDD%3e2.0.CO;2
Dickinson BC, Lin VS, Chang CJ (2013) Preparation and use of MitoPY1 for imaging hydrogen peroxide in mitochondria of live cells. Nat Protoc 8:1249–1259. https://doi.org/10.1038/nprot.2013.064
Samigullin DV, Khaziev EF, Zhilyakov NV et al (2017) Loading a calcium dye into frog nerve endings through the nerve stump: Calcium transient registration in the frog neuromuscular junction. J Vis Exp 2017:1–8. https://doi.org/10.3791/55122
Liu X, Wan Q, Zhao Z et al (2017) Microwave-assisted Diels-Alder reaction for rapid synthesis of luminescent nanodiamond with AIE-active dyes and their biomedical applications. Mater Chem Phys 197:256–265. https://doi.org/10.1016/j.matchemphys.2017.05.041
Elgemeie GH, Mohamed RA (2018) Microwave synthesis of fluorescent and luminescent dyes (1990–2017). J Mol Struct 1173:707–742. https://doi.org/10.1016/j.molstruc.2018.06.101
Rao VP, Jen AK-Y, Caldwell JB (1994) Rhodanine-methine as π-electron acceptor in second-order nonlinear optical chromophores. Tetrahedron Lett 35:3849–3852. https://doi.org/10.1016/S0040-4039(00)76683-4
Facchetti A, Beverina L, Van Der Boom ME et al (2006) Strategies for electrooptic film fabrication. Influence of pyrrole-pyridine-based dibranched chromophore architecture on covalent self-assembly, thin-film microstructure, and nonlinear optical response. J Am Chem Soc 128:2142–2153. https://doi.org/10.1021/ja057556c
Grabowski ZR, Rotkiewicz K, Rettig W (2003) Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures. Chem Rev 103:3899–4032. https://doi.org/10.1021/cr940745l
Thompson BC, Abboud KA, Reynolds JR et al (2005) Electrochromic conjugated N-salicylidene-aniline (anil) functionalized pyrrole and 2,5-dithienylpyrrole-based polymers. New J Chem 29:1128–1134. https://doi.org/10.1039/b504577k
Yang JX, Tao XT, Chun XY et al (2005) A facile synthesis and properties of multicarbazole molecules containing multiple vinylene bridges. J Am Chem Soc 127:3278–3279. https://doi.org/10.1021/ja043510s
Kimura M, Shiba T, Yamazaki M et al (2001) Construction of regulated nanospace around a porphyrin core. J Am Chem Soc 123:5636–5642. https://doi.org/10.1021/ja004312d
Chen S, Xu X, Liu Y et al (2005) Synthesis and characterization of n-type materials for non-doped organic red-light-emitting diodes. Adv Funct Mater 15:1541–1546. https://doi.org/10.1002/adfm.200500105
Liaw DJ, Wang KL, Chang FC et al (2007) Novel poly(pyridine imide) with pendent naphthalene groups: Synthesis and thermal, optical, electrochemical, electrochromic, and protonation characterization. J Polym Sci Part A Polym Chem 45:2367–2374. https://doi.org/10.1002/pola.21997
Liu G, Ling QD, Kang ET et al (2007) Bistable electrical switching and write-once read-many-times memory effect in a donor-acceptor containing polyfluorene derivative and its carbon nanotube composites. J Appl Phys 102:024502. https://doi.org/10.1063/1.2756386
Liu JG, Wang LF, Yang HX et al (2004) Synthesis and characterization of new polybenzimidazopyrrolones derived from pyridine-bridged aromatic tetraamines and dianhydrides. J Polym Sci Part A Polym Chem 42:1845–1856. https://doi.org/10.1002/pola.20030
Pan X, Liu S, Chan HSO, Ng SC (2005) Novel fluorescent carbazolyl-pyridinyl alternating copoloymers: Synthesis, characterization, and properties. Macromolecules 38:7629–7635. https://doi.org/10.1021/ma050425b
Sonntag M, Strohriegl P (2004) Novel 2,7-linked carbazole trimers as model compounds for conjugated carbazole polymers. Chem Mater 16:4736–4742. https://doi.org/10.1021/cm040142i
Wang KL, Liou WT, Liaw DJ, Chen WT (2008) A novel fluorescent poly(pyridine-imide) acid chemosensor. Dye Pigment 78:93–100. https://doi.org/10.1016/j.dyepig.2007.10.015
Wang KL, Liou WT, Liaw DJ, Huang ST (2008) High glass transition and thermal stability of new pyridine-containing polyimides: Effect of protonation on fluorescence. Polymer (Guildf) 49:1538–1546. https://doi.org/10.1016/j.polymer.2008.01.039
Zaami N, Slugovc C, Pogantsch A, Stelzer F (2004) Blue light emission from a fluorene-carbazole-fluorene trimer incorporated as the side chain into a polynorbornene. Macromol Chem Phys 205:523–529. https://doi.org/10.1002/macp.200300100
Dilek O, Bane SL (2011) Synthesis and spectroscopic characterization of fluorescent boron dipyrromethene-derived hydrazones. J Fluoresc 21:347–354. https://doi.org/10.1007/s10895-010-0723-0
Duan L, Chen Y, Jia J et al (2020) Dopant-free hole-transport materials based on 2,4,6-triarylpyridine for inverted planar perovskite solar cells. ACS Appl Energy Mater 3:1672–1683. https://doi.org/10.1021/acsaem.9b02152
Aloïse S, Pawlowska Z, Poizat O et al (2014) Excited-state dynamics of thiophene substituted betaine pyridinium compounds. Phys Chem Chem Phys 16:1460–1468. https://doi.org/10.1039/c3cp53614a
Reichardt C, Asharin-Fard S (1991) Chromoionophoric pyridinium-N-phenolate betaine dyes. Angew Chemie Int Ed English 30:558–559. https://doi.org/10.1002/anie.199105581
Jin XH, Chen C, Ren CX et al (2014) Bright white-light emission from a novel donor-acceptor organic molecule in the solid state via intermolecular charge transfer. Chem Commun 50:15878–15881. https://doi.org/10.1039/c4cc07063a
Costa JCS, Taveira RJS, Lima CFRAC et al (2016) Optical band gaps of organic semiconductor materials. Opt Mater (Amst) 58:51–60. https://doi.org/10.1016/j.optmat.2016.03.041
Kanakala MB, Yelamaggad CV (2021) Exceptional dual fluorescent, excited-state intramolecular proton-transfer (ESIPT) columnar liquid crystals characterized by J-stacking and large Stokes shifts. J Mol Liq 332:115879. https://doi.org/10.1016/j.molliq.2021.115879
Awuah SG, Polreis J, Prakash J et al (2011) New pyran dyes for dye-sensitized solar cells. J Photochem Photobiol A Chem 224:116–122. https://doi.org/10.1016/j.jphotochem.2011.09.014
Thorat KG, Kamble P, Ray AK, Sekar N (2015) Novel pyrromethene dyes with N-ethyl carbazole at the meso position: a comprehensive photophysical, lasing, photostability and TD-DFT study. Phys Chem Chem Phys 17:17221–17236. https://doi.org/10.1039/c5cp01741f
Panda S, Jat RS, Fayaz A et al (2020) Conjugated small organic molecules: Synthesis and characterization of 4-arylpyrazole-decorated dibenzothiophenes. New J Chem 44:8944–8951. https://doi.org/10.1039/d0nj01887b
Maroń A, Kula S, Szlapa-Kula A et al (2017) 2,2′:6′,2′′-Terpyridine Analogues: Structural, electrochemical, and photophysical properties of 2,6-Di(thiazol-2-yl)pyridine derivatives. European J Org Chem 2017:2730–2745. https://doi.org/10.1002/ejoc.201700141
Dineshkumar S, Muthusamy A (2017) Investigation of aggregation induced emission in 4-hydroxy-3- methoxybenzaldehyde azine and polyazine towards application in (opto) electronics: Synthesis, characterization, photophysical and electrical properties. Des Monomers Polym 20:234–249. https://doi.org/10.1080/15685551.2016.1231039
Kagatikar S, Sunil D, Kekuda D et al (2020) New salicylaldehyde azine esters: Structural, aggregation induced fluorescence, electrochemical and theoretical studies. J Mol Liq 318:114029. https://doi.org/10.1016/j.molliq.2020.114029
Bochevarov AD, Harder E, Hughes TF et al (2013) Jaguar: A high-performance quantum chemistry software program with strengths in life and materials sciences. Int J Quantum Chem 113:2110–2142. https://doi.org/10.1002/qua.24481
Acknowledgements
The authors thank Mrs. K. N. Vasudha for DSC analyses; Mr. Dheeraj Devadiga for helping to carry out the NMR and DFT analyses.
Funding
This research was supported by the Science & Engineering Research Board (SERB) under Core Research Grant (Project File no.: CRG/2020/003151), Govt. of India, New Delhi.
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Deepak Devadiga: Conceptualization, Performed experiments, collected data, chemical characterization studies and prepared draft manuscript. Ahipa TN: Conceptualization, Methodology, and manuscript reviewing. Vanishree Bhat S.: POM, DSC, manuscript reviewing. Sandeep Kumar: POM, DSC, manuscript reviewing.
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Devadiga, D., Ahipa, T.N., Bhat, S.V. et al. New Luminescent Pyridine-based Disc type Molecules: Synthesis, Photophysical, Electrochemical, and DFT studies. J Fluoresc 33, 445–452 (2023). https://doi.org/10.1007/s10895-022-03090-2
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DOI: https://doi.org/10.1007/s10895-022-03090-2