Abstract
Two-photon absorption of a series of symmetrical diketopyrrolopyrrole (DPP) derivatives is studied by means of density functional theory applied to second-order response function. Several important issues in modeling are highlighted which must be addressed for a reliable reproduction of the experimental results. A comparison of the theoretical results with the experimental ones indicates that the computed two-photon absorption (TPA) cross sections show a good agreement for the three-state model in case of symmetrical quadrupolar DPP derivatives with donor ending groups. Although the results of TPA cross section observed for the systems with strong electron accepting ending groups seem to be overestimated for the three-state model. At the same time using an algorithm for the direct calculation of the third-order processes by the solving dynamic coupled-perturbed Hartree–Fock equation shows relatively good qualitative results for both donor and acceptor ending groups; however, it was found to be less accurate quantitatively for the already published experimental results. Thus, to obtain a valid overview, supposedly, both methods have to be considered. In general, in the present paper, a strategy toward molecular tailoring of large TPA cross-sectional materials is described, which can be extremely useful tool to predict materials’ properties prior to synthesis and measurements.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Andrews DL (2014) Molecular, photophysics and spectroscopy. Morgan & Claypool Publishers, San Rafael. ISBN 978-1-627-05288-7
Barzoukas M, Blanchard-Desce M (2000) Molecular engineering of push–pull dipolar and quadrupolar molecules for two-photon absorption: a multivalence-bond states approach. J Chem Phys 113:3951–3959. https://doi.org/10.1063/1.1288367
Beerepoot MTP, Friese DH, List NH, Kongsted J, Ruud K (2015) Benchmarking two-photon absorption cross sections: performance of CC2 and CAM-B3LYP. Phys Chem Chem Phys 17:19306–19314. https://doi.org/10.1039/C5CP03241E
Bjorgaard JA, Sifain AE, Nelson T et al (2016) Two-photon absorption in conjugated energetic molecules. J Phys Chem A 120:4455–4464. https://doi.org/10.1021/acs.jpca.6b03136
Brütting W, Adachi CH, Holmes RJD (2012) Physics of organic semiconductors. Wiley, Weinheim. ISBN: 9783527410538
Chernyak V, Tretiak S, Mukamel S (2000) Electronic versus vibrational optical nonlinearities of push-pull polymers. Chem Phys Lett 319:261–264. https://doi.org/10.1016/S0009-2614(00)00115-9
Cho MJ, Shin J, Yoon SH, Lee TW, Kaur M, Choi DH (2013) A high-mobility terselenophene and diketopyrrolopyrrole containing copolymer in solution-processed thin film transistors. Chem Commun 49:7132–7134. https://doi.org/10.1039/c3cc43742f
Corns SN, Partington SM, Towns AD (2009) Industrial organic photochromic dyes. Color Technol 125:249–261. https://doi.org/10.1111/j.1478-4408.2009.00204.x
Cronstrand P, Luo Y, Ågren H (2002a) Effects of dipole alignment and channel interference on two-photon absorption cross sections of two-dimensional charge-transfer systems. J Chem Phys 117:11102–11106. https://doi.org/10.1063/1.1522408
Cronstrand P, Luo Y, Ågren H (2002b) Generalized few-state models for two-photon absorption of conjugated molecules. Chem Phys Lett 352:262–269. https://doi.org/10.1016/S0009-2614(01)01454-3
Cronstrand P, Norman P, Luo Y, Ågren H (2004) Few-states models for three-photon absorption. J Chem Phys 121:2020–2029. https://doi.org/10.1063/1.1767516
Cui Y, Yang Ch, Yao H, Zhu J, Wang Y, Jia G, Gao F, Hou J (2017) Efficient semitransparent organic solar cells with tunable color enabled by an ultralow-bandgap nonfullerene acceptor. Adv Mater 29:1703080. https://doi.org/10.1002/adma.201703080
Cumpston BH, Ananthavel SP, Barlow S et al (1999) Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication. Nature 398:51–54. https://doi.org/10.1038/17989
Data P, Kurowska A, Pluczyk S et al (2016) Exciplex enhancement as a tool to increase OLED device efficiency. J Phys Chem C 120:2070–2078. https://doi.org/10.1021/acs.jpcc.5b11263
Denk W, Strickler JH, Webb WW (1990) Two-photon laser scanning fluorescence microscopy. Science 248:73–76 (PMID: 2321027)
Eckstein JN, Ferguson AI, Hänsch TW (1978) High-resolution two-photon spectroscopy with picosecond light pulses. Phys Rev Lett 40:847. https://doi.org/10.1103/PhysRevLett.40.847
Ehrlich JE, Wu XL, Lee IYS, Hu ZY, Röckel H, Marder SR, Perry JW (1997) Two-photon absorption and broadband optical limiting with bis-donor stilbenes. Opt Lett 22:1843. https://doi.org/10.1364/OL.22.001843
Fischer MKR, Wenger S, Wang M, Mishra A, Zakeeruddin SM, Grätzel M, Bäuerle P (2010) D–π—a sensitizers for dye-sensitized solar cells: linear vs branched oligothiophenes. Chem Mater 22:1836–1845. https://doi.org/10.1021/cm903542v
Frisch MJ, Trucks GW, Schlegel HB et al (2016) Gaussian, Inc., Wallingford
Ftouni H, Bolze F, De Rocquigny H, Nicoud J-F (2013) Functionalized two-photon absorbing diketopyrrolopyrrole-based fluorophores for living cells fluorescent microscopy. Bioconj Chem 24:942–950. https://doi.org/10.1021/bc300623q
Geffroy B, Le Roy P, Prat Ch (2006) Organic light-emitting diode (OLED) technology: materials, devices and display technologies. Polym Int 55:572–582. https://doi.org/10.1002/pi.1974
Göppert-Mayer M (1931) Über Elementarakte mit zwei Quantensprüngen. Ann Phys 401:273–294. https://doi.org/10.1002/andp.19314010303
Grzybowski M, Gryko DT (2015) Diketopyrrolopyrroles: synthesis, reactivity, and optical properties. Adv Opt Mater 3:280–320. https://doi.org/10.1002/adom.201400559
Guo JD, Wang CK, Luo Y, Ågren H (2003) Influence of electron-acceptor strength on the resonant two-photon absorption cross sections of diphenylaminofluorene-based chromophores. Phys Chem Chem Phys 5:3869–3873. https://doi.org/10.1039/B307732B
Guo EQ, Ren PH, Zhang YL, Zhang HCh, Yang WJ (2009) Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence. Chem Commun 39:5859–5861. https://doi.org/10.1039/b911808j
Hahn S, Kim D, Cho M (1999) Nonlinear optical properties of the linear quadrupolar molecule: structure—function relationship based on a three-state model. J Phys Chem B 103:8221–8229. https://doi.org/10.1021/jp9836933
Hu Z, Wang W, Khadka VS, Galipeau DW, Yan XZ (2011) Quantum mechanical modelling and calculation of two-photon absorption properties of new class ‘Λ’-shaped conjugated molecules. Mol Simul 37:431–439. https://doi.org/10.1080/08927022.2010.550287
Jiang T, Li D, Hang Y, Gao Y, Zhang H, Zhao X, Li X, Li B, Qian J, Hua J (2016) Tetraphenylethene end-capped diketopyrrolopyrrole fluorogens with AIE and large two-photon absorption cross-sections features and application in bioimaging. Dyes Pigm 133:201–213. https://doi.org/10.1016/j.dyepig.2016.05.043
Kaltenbrunner M, White MS, Głowacki ED, Sekitani T, Someya T, Sariciftci NS, Bauer S (2012) Ultrathin and lightweight organic solar cells with high flexibility. Nat Commun 3:770. https://doi.org/10.1038/ncomms1772
Kaur M, Choi DH (2015) Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications. Chem Soc Rev 44:58–77. https://doi.org/10.1039/C4CS00248B
Kim DY, Ahn TK, Kwon JH, Kim D, Ikeue T, Aratani N, Osuka A, Shigeiwa M, Maeda S (2005) Large two-photon absorption (TPA) cross-section of directly linked fused diporphyrins. J Phys Chem A 109:2996–2999. https://doi.org/10.1021/jp050747h
Kovalenko A, Yumusak C, Heinrichova P et al (2017) Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials. J Mater Chem C 5:4716–4723. https://doi.org/10.1039/C6TC05076J
Li Y, Zheng M, Wang J, Gao Y, Zhang B, Yang W (2014) Two-photon absorption and fluorescence fluoride-sensing properties of N-octyl-3,6-bis[4-(4-(diphenylamino)phenyl)phenyl]-1,4-diketo-pyrrolo[3,4-c]pyrrole. Dyes Pigm 104:97–101. https://doi.org/10.1016/j.dyepig.2013.12.031
Lin T-Ch, Liu Ch-Y, Huang B-R, Lin J-H, Shen Y-K, Wu Ch-Y (2013) Synthesis and two-photon absorption properties of star-shaped chromophores derived from functionalized fluorene units. Eur J Org Chem 2013:498–508. https://doi.org/10.1002/ejoc.201201236
Liu Zh, Zhang K, Sun Q, Zhang Zh, Tang L, Xue S, Chen D, Zhang H, Yang W (2018) Synthesis and remarkable mechano- and thermo-hypsochromic luminescence of a new type of DPP-based derivative. J Mater Chem C 6:1377–1383. https://doi.org/10.1039/C7TC04698G
Lu L, Zheng T, Wu Q, Schneider AM, Zhao D, Yu L (2015) Recent advances in bulk heterojunction polymer solar cells. Chem Rev 115:12666–12731. https://doi.org/10.1021/acs.chemrev.5b00098
Maglione C, Carella A, Centore R, Chávez P, Léveque P, Fall S, Leclerc N (2017) Novel low bandgap phenothiazine functionalized DPP derivatives prepared by direct heteroarylation: application in bulk heterojunction organic solar cells. Dyes Pigm 141:169–178. https://doi.org/10.1016/j.dyepig.2017.02.012
Michiko T, Chisaka J, Watanabe M (2014) Jpn. KokaiTokkyoKoho. JP 2014187154. http://www.conceptsengine.com/patent/grant/0005907289
Miller CE, Wasielewski MR, Schatz GC (2017) Modeling singlet fission in rylene and diketopyrrolopyrrole derivatives: the role of the charge transfer state in superexchange and excimer formation. J Phys Chem C 121:10345–10350. https://doi.org/10.1021/acs.jpcc.7b02697
Mongin O, Porres L, Charlot M, Katan C, Blanchard-Desce M (2007) Synthesis, fluorescence, and two-photon absorption of a series of elongated rodlike and banana-shaped quadrupolar fluorophores: a comprehensive study of structure-property relationships. Chem Eur J 13:1481–1498. https://doi.org/10.1002/chem.200600689
Moran AM, Kelley AM, Tretiak S (2003) Excited state molecular dynamics simulations of nonlinear push–pull chromophores. Chem Phys Lett 367:293–307. https://doi.org/10.1016/S0009-2614(02)01583-X
Mueller ChJ, Brendel M, Ruckdeschel P, Pflaum J, Thelakkat M (2015) Diketopyrrolopyrroles with a distinct energy level cascade for efficient charge carrier generation in organic solar cells. Adv Energy Mater 5:1500914. https://doi.org/10.1002/aenm.201500914
Nayyar IH, Masunov AE, Tretiak S (2013) Comparison of TD-DFT methods for the calculation of two-photon absorption spectra of oligophenylvinylenes. J Phys Chem C 117:18170–18189. https://doi.org/10.1021/jp403981d
Norman P, Luo Y, Ågren H (1999) Large two-photon absorption cross sections in two-dimensional, charge-transfer, cumulene-containing aromatic molecules. J Chem Phys 111:7758–7765. https://doi.org/10.1063/1.480111
Ohta K, Kamada K (2006) Theoretical investigation of two-photon absorption allowed excited states in symmetrically substituted diacetylenes by ab initio molecular-orbital method. J Chem Phys 124:124303. https://doi.org/10.1063/1.2181973
Otani J, Yamamoto H, Dan N, Iqbal A, Moretti R (2001) European Patenet Application EP 1,087,006
Parthenopoulos DA, Rentzepis PM (1989) Three-dimensional optical storage memory. Science 245:843–845. https://doi.org/10.1126/science.245.4920.843
Peticolas WL (1967) Multiphoton spectroscopy. Annu Rev Phys Chem 18:233. https://doi.org/10.1146/annurev.pc.18.100167.001313
Poulsen TD, Ogilby PR, Mikkelsen KV (2001) A quantum mechanical method for calculating nonlinear optical properties of condensed phase molecules coupled to a molecular mechanics field: a quadratic multiconfigurational self-consistent-field/molecular mechanics response method. J Chem Phys 115:7843–7851. https://doi.org/10.1063/1.1400138
Prabhu RN, Ramesh R (2013) Synthesis and structural characterization of palladium(II) thiosemicarbazone complex: application to the Buchwald–Hartwig amination reaction. Tetrahedron Lett 54:1120–1124. https://doi.org/10.1016/j.tetlet.2012.12.070
Purc A, Sobczyk K, Sakagami Y, Ando A, Kamada K, Gryko DT (2015) Strategy towards large two-photon absorption cross-sections for diketopyrrolopyrroles. J Mater Chem C 3:742–749. https://doi.org/10.1039/C4TC02375G
Qiao Y, Guo Y, Yu Ch, Zhang F, Xu W, Liu Y, Zhu D (2012) Diketopyrrolopyrrole-containing quinoidal small molecules for high-performance, air-stable, and solution-processable n-channel organic field-effect transistors. J Am Chem Soc 134:4084–4087. https://doi.org/10.1021/ja3003183
Rampon DS, Wessjohann LA, Schneider PH (2014) Palladium-catalyzed direct arylation of selenophene. J Org Chem 79:5987–5992. https://doi.org/10.1021/jo500094t
Rizzo A, Coriani S, Ruud K (2012) Response function theory computational approaches to linear and nonlinear optical spectroscopy. i Computational Strategies for Spectroscopy. In:Barone V (eds) Molecules to Nanosystems, Wiley, pp 77–135
Ros MB (2008) Organic materials for nonlinear optics. In: Novoa JJ, Braga D, Addadi L (eds) NATO science for peace and security series B: physics and biophysics. Springer, Dordrecht
Rubio-Pons O, Luo Y, Ågren H (2006) Effects of conjugation length, electron donor and acceptor strengths on two-photon absorption cross sections of asymmetric zinc-porphyrin derivatives. J Chem Phys 124:94310–94314. https://doi.org/10.1063/1.2178790
Rumi M, Ehrlich JE, Heikal AA, Perry JW, Barlow S, Hu ZY, McCord-Maughon D, Parker TC, Rockel H, Thayumana-van SR, Marder S, Beljonne D, Bredas JL (2000) Two-photon absorbing chromophores: bis-donor diphenylpolyene and bis(styryl)benzene derivatives. J Am Chem Soc 122:9500–9510. https://doi.org/10.1021/ja994497s
Schmitt J, Heitz V, Sour A, Bolze F, Ftouni H, Nicoud J-F, Flamigni L, Ventura B (2015) Diketopyrrolopyrrole-porphyrin conjugates with high two-photon absorption and singlet oxygen generation for two-photon photodynamic therapy. Angew Chem Int Ed 54:169–173. https://doi.org/10.1002/anie.201407537
Sperber P, Penzkofer A (1986) S0–Sn two-photon absorption dynamics of rhodamine dyes. Opt Quantum Electron 18:381–401. https://doi.org/10.1007/BF02032565
Strehmel B, Amthor S, Schelter J, Lambert C (2005) Two-photon absorption of bis[4-(N,N-diphenylamino)phenylethynyl]arenes. ChemPhysChem 6:893–896. https://doi.org/10.1002/cphc.200400538
Sutherland RL (1996) Handbook of nonlinear optics. Marcel Dekker, New York. ISBN 9780203912539
Tamano M, Chisaka J (2016) Jpn. Tokkyo Koho. JP 5907289. http://www.conceptsengine.com/patent/grant/0005907289
Terenziani F, Morone M, Gmouh S, Blanchard-Desce M (2006a) Linear and two-photon absorption properties of interacting polar chromophores: standard and unconventional effects. Chem Phys Chem 7:685–696. https://doi.org/10.1002/cphc.200500536
Terenziani F, Painelli A, Katan C, Charlot M, Blanchard-Desce M (2006b) Charge instability in quadrupolar chromophores: symmetry breaking and solvatochromism. J Am Chem Soc 128:15742–15755. https://doi.org/10.1021/ja064521j
Terenziani F, Katan C, Badaeva E, Tretiak S, Blanchard-Desce M (2008) Enhanced two-photon absorption of organic chromophores: theoretical and experimental assessments. Adv Mater 20:4641–4678. https://doi.org/10.1002/adma.200800402
Tutt LW, Boggess TF (1993) A review of optical limiting mechanisms and devices using organics, fullerenes, semiconductors and other materials. Prog Quantum Electron 17:299–338. https://doi.org/10.1016/0079-6727(93)90004-s
Wang CK, Macak P, Luo Y, Agren H (2001) Effects of π centers and symmetry on two-photon absorption cross sections of organic chromophores. J Chem Phys 114:9813–9820. https://doi.org/10.1063/1.1371258
Wang CK, Zhao K, Su Y, Ren Y, Zhao X, Luo Y (2003) Solvent effects on the electronic structure of a newly synthesized two-photon polymerization initiator. J Chem Phys 119:1208–1213. https://doi.org/10.1063/1.1579680
Weiter M, Salyk O, Bednar P, Vala M, Navratil J, Zmeskal O, Vynuchal J, Lunak S (2009) Morphology and properties of thin films of diketopyrrolopyrrole derivatives. Mater Sci Eng B 165:148–152. https://doi.org/10.1016/j.mseb.2009.09.017
Xu Ch, Webb WW (1996) Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B 13:481–491. https://doi.org/10.1364/JOSAB.13.000481
Xu J, Zhang S, Wu S, Bi S, Li X, Lu Y, Wang L (2017) Rational synthesis and comparative investigation on a series of fluorinated aryl substituted diketopyrrolopyrrole. Tetrahedron 73:494–499. https://doi.org/10.1016/j.tet.2016.12.021
Yang C, Zheng M, Li Y, Zhang B, Li J, Bu L, Liu W, Sun M, Zhang H, Tao Y, Xue S, Yang W (2013) N-Monoalkylated 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrroles as effective one- and two-photon fluorescence chemosensors for fluoride anions. J Mater Chem A 1:5172–5178. https://doi.org/10.1039/C3TA00160A
Yang C, Zheng M, Li Y, Zhang D, Xue S, Yang W (2014) Poly(1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole-alt − 3,6-carbazole/2,7-fluorene) as high-performance two-photon dyes. J Polym Sci Part A Polym Chem 52:944–951. https://doi.org/10.1002/pola.27074
Yang J, Tan H, Li D, Jiang T, Gao Y, Li B, Qu X, Hua J (2016) Synthesis, two-photon absorption and aggregation-induced emission properties of multi-branched triphenylamine derivatives based on diketopyrrolopyrrole for bioimaging. RSC Adv 6:58434–58442. https://doi.org/10.1039/C6RA11269B
Yi HT, Payne MM, Anthony JE, Podzorov V (2012) Ultra-flexible solution-processed organic field-effect transistors. Nat Commun 3:1259. https://doi.org/10.1038/ncomms2263
Ying S, Chen M, Liu Zh, Zhang K, Pan Y, Xue S, Yang W (2016) 9-Anthryl-capped DPP-based dyes: aryl spacing induced differential optical properties. J Mater Chem C 4:8006–8013
Ying S, Chen M, Liu Zh, Zheng M, Zhang H, Xue S, Yang W (2017) Unusual mechanohypsochromic luminescence and unique bidirectional thermofluorochromism of long-alkylated simple DPP dyes. J Mater Chem C 5:5994–5998. https://doi.org/10.1039/C7TC01453H
Yoon WS, Park SK, Cho I, Oh JA, Kim JH, Park SY (2013) High-mobility n-type organic transistors based on a crystallized diketopyrrolopyrrole derivative. Adv Funct Mater 23:3519–3524. https://doi.org/10.1002/adfm.201203065
Zhang B, Zhang H, Li X, Li W, Sun P, Yang W (2011) Synthesis, characterization, and large two-photon absorption cross sections of solid red-emitting 1,4-diketo-3,6-diphenylpyrrolo[3, 4-c]pyrrole/3, 6-carbazole/terfluorene copolymers. J Polym Sci Part A Polym Chem 49:3048–3057. https://doi.org/10.1002/pola.24741
Zhang K, Chen M, Liu Zh, Ying S, Zhang H, Xue S, Yang W (2018) Two-photon absorption and mechanofluorochromic properties of 1,4-diketo-2,5-dibutyl-3,6-bis(4-(carbazol-N-yl)phenyl)pyrrolo[3,4-c]pyrrole. J Lumin 194:588–593. https://doi.org/10.1016/j.jlumin.2017.09.018
Zhao K (2007) Theoretical study of light-molecule nonlinear interactions. Ph.D. thesis, Department of Theoretical Chemistry, Royal Institute of Technology, Stockholm
Zou Y, Yue G, Xu J, Zhou JS (2014) General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand. Eur J Org Chem 2014:5901–5905. https://doi.org/10.1002/ejoc.201402915
Acknowledgements
This work was supported by the Czech Science Foundation Grant no. 17-21105S. Research infrastructure was supported by project no. REG LO1211 from the National Programme for Sustainability I (MEYS CR).
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
Kovalenko, A., Vala, M., Ciganek, M. et al. Design rules for the large two-photon absorption diketopyrrolopyrrole-based quadrupolar symmetrical chromophores. Chem. Pap. 72, 3033–3042 (2018). https://doi.org/10.1007/s11696-018-0530-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-018-0530-7