Abstract
This paper presents a variety of conjugated derivatives with different number of arms (4-styryl-triphenylamine: C1, 4, 4′-di-styryltriphenylamine: C2, 4, 4′, 4″-tri-styryltriphenylamine: C3). The linear absorption and fluorescence maxima and the molar extinction coefficients are in the order of C1<C2<C3 in various solvents. Two-photon absorption (TPA) up-converted emission of the derivatives were determined with Ti:sapphire femtosecond laser. The maximal TPA emission wavelength and the two-photon absorption cross section of the derivatives are also in the order of C1<C2<C3 in various solvents. The dipole moment changes of the derivatives between the excited state and the ground state were estimated from experiment, and they are in the order of C1<C2<C3, which is confirmed further by the molecular geometry optimization of the derivatives. The electron density distribution and the energy levels of the frontier orbital of the derivatives were analyzed. The cyclic voltammograms of the derivatives were performed and discussed.
Similar content being viewed by others
References
Taki M, Wolford JL, O’Halloran TV (2004) Emission ratiometric imaging of intracellular zinc: design of a Benzoxazole fluorescent sensor and its application in two-photon microscopy. J Am Chem Soc 126(3):712–713
Farruggia G, Iotti S, Prodi L, Montalti M, Zaccheroni N, Savage PB, Trapani V, Sale P, Wolf FI (2006) 8-hydroxyquinoline derivatives as fluorescent sensors for magnesium in living cells. J Am Chem Soc 128(1):344–350
Rice WL, Kaplan DL, Georgakoudi I (2007) Quantitative biorkers of stem cell differentiation based on intrinsic two-photon excited fluorescence. J Biomed Opt 12(6):060504
Wu YC, Qu JY (2005) Two-photon autofluorescence spectroscopy and second-harmonic generation of epithelial tissue. Opt Lett 30(22):3045–3047
(a) Tokar VP, Losytskyy MY, Ohulchanskyy TY, Kryvorotenko DV, Kovalska VB, Balanda AO, Dmytruk IM, Prokopets VM, Yarmoluk SM, Yashchuk VM(2010) Styryl dyes as two-photon excited fluorescent probes for DNA detection and two-photon laser scanning fluorescence microscopy of living cells. J Fluorescence 10.1007/s10895-010-0630-4, available in web. (b) Liu B, Zhang HL, Liu J, Huang ZL, Zhao YD, Luo QM (2007) Acetylene-substituted two-photon absorbing molecules with rigid elongated Pi-conjugation: synthesis, spectroscopic properties and two-photon fluorescence cell imaging applications. Journal of Fluorescence 17(5): 573–579 (c) Picot A, D’Aléo A, Baldeck PL, Grichine A, Duperray A, Andraud C, Maury O (2008) Long-lived two-photon excited luminescence of water-soluble europium complex: applications in biological imaging using two-photon scanning microscopy. J Am Chem Soc 130 (5):1532–1533
Law GL, Wong KL, Man C, Wong WT, Tsao SW, Lam M, Lam P (2008) Emissive terbium probe for multiphoton in vitro cell imaging. J Am Chem Soc 130(12):3714–3715
Kim S, Ohulchanskyy TY, Pudavar HE, Pandey RK, Prasad PN (2007) Organically modified silica nanoparticles co-encapsulating photosensitizing drug and aggregation-enhanced two-photon absorbing fluorescent dye aggregates for two-photon photodynamic therapy. J Am Chem Soc 129(9):2669–2675
Karotki A, Khurana M, Lepock JR, Wilson BC (2006) Simultaneous two-photon excitation of photofrin in relation to photodynamic therapy. Photochem Photobiol 82(2):443–452
Babgi B, Rigamonti L, Cifuentes MP, Corkery TC, Randles MD, Schwich T, Petrie S, Stranger R, Teshome A, Asselberghs I, Clays K, Samoc M, Humphrey MG (2009) Length-dependent convergence and saturation behavior of electrochemical, linear optical, quadratic nonlinear optical, and cubic nonlinear optical properties of dipolar alkynylruthenium complexes with oligo(phenyleneethynylene) bridges. J Am Chem Soc 131(29):10293–10307
Liu CG, Guan W, Yan LK, Su ZM, Song P, Wang EB (2009) Second-order nonlinear optical properties of transition-metal-trisubstituted polyoxometalate−diphosphate complexes: a donor−conjugated bridge−acceptor paradigm for totally inorganic nonlinear optical materials. J Phys Chem C 113(45):19672–19676
(a) Reinhardt BA (1998) Highly active two-photon dyes: design, synthesis, and characterization toward application. Chem Mater 10(7): 1863–1874 (b) Meltola NJ, Vaarno J, Soini AE (2005) Dipyrrylmetheneboron difluorides as labels in two-photon excited fluorometry. Part II–nucleic acid hybridization assays. J Fluorescence 15(3):233–242
Belfield KD, Liu Y, Negres RA, Fan M, Pan G, Hagan DJ, Hernandez FE (2002) Two-photon photochromism of an organic material for holographic recording. Chem Mater 14(9):3663–3667
He GS, Dai TC, Lin JM, Prasad PN, Kannan R, Dombroskie AG, Vaia RA, Tan LS (2004) Degenerate two-photon-absorption spectral studies of highly two-photon active organic chromophores. J Chem Phys 120(11):5275–5284
Bordeau G, Lartia R, Metge G, Fiorini-Debuisschert C, Charra F, Teulade-Fichou MP (2008) Trinaphthylamines as robust organic materials for two-photon-induced fluorescence. J Am Chem Soc 130(50):16836–16837
Williams-Harry M, Bhaskar A, Ramakrishna G, Goodson T, Imamura M, Mawatari A, Nakao K, Enozawa H, Nishinaga T, Iyoda M (2008) Giant thienylene-acetylene-ethylene macrocycles with large two-photon absorption cross section and semishape-persistence. J Am Chem Soc 130(11):3252–3253
Beverina L, Crippa M, Landenna M, Ruffo R, Salice P, Silvestri F, Versari S, Villa A, Ciaffoni L, Collini E, Ferrante C, Bradamante S, Mari CM, Bozio R, Pagani GA (2008) Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: design, synthesis, and characterization. J Am Chem Soc 130(6):1894–1902
Pawlicki M, Collins HA, Denning RG, Anderson HL (2009) Two-photon absorption and the design of two-photon dyes. Angew Chem Int Ed 48(18):3244–3266
Beverina L, Crippa M, Salice P, Ruffo R, Ferrante C, Fortunati I, Signorini R, Mari CM, Bozio R, Facchetti A, Pagani GA (2008) Indolic squaraines as two-photon absorbing dyes in the visible region: x-ray structure, electrochemical, and nonlinear optical characterization. Chem Mater 20(10):3242–3244
Porrès L, Mongin O, Katan C, Charlot M, Pons T, Mertz J, Blanchard-Desce M (2004) Enhanced two-photon absorption with novel octupolar propeller-shaped fluorophores derived from triphenylamine. Org Lett 6(1):47–50
Segura JL, Gómez R, Martín N, Guldi DM (2001) Synthesis of photo- and electroactive stilbenoid dendrimers carrying dibutylamino peripheral groups. Org Lett 3(17):2645–2648
Perrin DD, Armarego WLF, Perrin DR (1966) Purification of laboratory chemicals. Pergamon, New York
Grabolle M, Spieles M, Lesnyak V, Gaponik N, Eychmller A, Resch-Geer U (2009) Determination of the fluorescence quantum yield of quantum dots: suitable procedures and achievable uncertainties. Anal Chem 81(15):6285–6294
FischerM GJ (1996) Fluorescence quantum yield of rhodamine 6G in ethanol as a function of concentration using thermal lens spectrometry. Chem Phys Lett 260(1–2):115–118
Maus M, Reitigg W, Bonafoux D, Lapouyade R (1999) Photoinduced intramolecular charge transfer in a series of differently twisted donor−acceptor biphenyls as revealed by fluorescence. J Phys Chem A 103(18):3388–3401
Lukeman M, Veal D, Wan P, Ranjit V, Munasinghe N, Corrie JE (2004) Photogeneration of 1, 5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution. Can J Chem 82(14):240–253
Xu C, 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(3):481–491
Albota MA, Xu C, Webb WW (1998) Two-photon fluorescence excitation cross sections of biomolecular probes from 690 to 960 nm. Appl Opt 37(31):7352–7356
Hyperchem 8.0 Package (2002). Hyperchem Inc., Gainesville FL, USA
Drwar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 107(13):3902–3909
Mallegol T, Gmouh S, Meziane MAA, Blanchard-Desce M, Mongin O (2005) Practical and efficient synthesis of tris(4-formylphenyl)amine, a key building block in materials chemistry. Synthesis 2005(11):1771–1774
Chiang WY, Laane J (1994) Fluorescence spectra and torsional potential functions for trans-stilbene in its S0 and S1 (π, π*) electronic states. J Chem Phys 100(12):8755–8768
Wang S, Kim SH (2009) Photophysical and electrochemical properties of D–π–A type solvatofluorchromic isophorone dye for pH molecular switch. Current Appl Phys 9(4):783–787
Albota M, Beljonne D, Brédas JL, Ehrlich JE, Fu JY, Heikal AA, Hess SE, Kogej T, Levin MD, Marder SR, McCord-Maughon D, Perry JW, Röckel H, Rumi M, Subramaniam G, Webb WW, Wu XL, Xu C (1998) Design of organic molecules with large two-photon absorption cross sections. Science 281(11):1653–1656
Nguyen KA, Day PN, Pachtera R (2007) Effects of solvation on one- and two-photon spectra of coumarin derivatives: a time-dependent density functional theory study. J Chem Phys 126(9):094303–094313
Guo JD, Wang CK, Luo Y, Agren H (2003) Influence of electron-acceptor strength on the resonant two-photon absorption cross sections of diphenylaminofluorene-based chromophores. Phys Chem Chem Phys 5(18):3869–3873
He GS, Tan LS, Zheng QD, Prasad PN (2008) Multiphoton absorbing materials: molecular designs, characterizations, and applications. Chem Rev 108(4):1245–1330
Lippert VEZ (1957) Spektroskopische bistimmung des dipolmomentes aromatischer Verbindungen Im Ersten Angeregten Singulettzustand. Z Electrochem 61:962
Lakowicz JR (1999) Principles of fluorescence spectroscopy. Kluwer Academic, New York
Aoki K, Guo Y, Chen JY (2009) Diffusion-controlled currents in viscous solutions of polyethylene glycols. J Electroanal Chem 629(1–2):73–77
Domagalska BW, Wilk KA, Wysocki S (2003) Experimental and theoretical studies on solvent effects of amphiphilic conjugated polyenals. Phys Chem Chem Phys 5(4):696–702
Liu J, Tu G, Zhou Q, Cheng Y, Geng Y, Wang L, Ma D, Jing X, Wang F (2006) Highly efficient green light emitting polyfluorene incorporated with 4-diphenylamino-1, 8-naphthalimide as green dopant. J Mater Chem 16(15):1431–1438
Bard AJ, Faulkner LA (1984) Electrochemical methods-fundamentals and applications. Wiley, New York
Acknowledgements
The authors appreciate financial support from National Natural Science Foundation of China (Nos. 20776165, 20702065, 20872184). We would thank “the Foundation of Chongqing Science and Technology Commission” (CSTC2008BA4020, CSTC2009BB4216). H. Li thanks “A Foundation for the Author of National Excellent Doctoral Dissertation of PR China (200735)”, and thanks supports from the Key Laboratory of Functional Crystals and Laser Technology, TIPC, Chinese Academy of Sciences. We thank Dr. X. Chen for helpful discussion on molecular geometry optimization. We also thank “Innovative Talent Training Project, the Third State of ‘211 Project, S-09103’, Chongqing University.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Yang, L., Gao, F., Liu, J. et al. A Comprehensive Investigation on the Cooperative Branch Effect on the Optical Properties of Novel Conjugated Compounds. J Fluoresc 21, 545–554 (2011). https://doi.org/10.1007/s10895-010-0741-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-010-0741-y