Abstract
Two novel terpyridine-based chromophores with D-A (D = donor, A = acceptor) structural model containing modified triphenylamine moiety (L 1 and L 2) have been conveniently synthesized via formylation and reduction in satisfactory yields, and fully characterized. The single crystals of them were obtained and determined by X-ray diffraction analysis. The relationships between structure and photophysical properties of the two chromophores were investigated both experimentally and theoretically. The measured maximum TPA cross-sections per molecular weight (δ max/MW) of the chromophores are 0.63 GM/(g mol) (L 1) and 0.72 GM/(g mol) (L 2), respectively, in DMF as a high polar solvent. The results indicate that the value of δ max/MW could be well tuned by the intramolecular charge transfer (ICT), which could be realized by introducing additional electron-donor/acceptor groups.
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Göppert-Mayer M. Über elementarakte mit zwei Quantensprüngen. Ann Phys (Leipzig), 1931, 9:273–294
Kaiser W, Garrett CGB. Two-photon excitation in CaF2:Eu2+. Phys Rev Lett, 1961:229–231
Cumpston BH, Ananthavel SP, Barlow S, Dyer DL, Ehrlich JE, Erskine LL, Heikal AA, Kuebler SM, Lee IYS, Dianne MM, Qin JQ, Röckel H, Rumi M, Wu XL, Marder SR, Perry JW. Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication. Nature, 1999, 398:51–54
Yuan WF, Sun L, Tang HH, Wen YQ, Jiang GY, Huang WH, Jiang L, Song YL, Tian H, Zhu DB. A novel thermally stable spironaphthoxazine and its application in rewritable high density optical data storage. Adv Mater, 2005, 17:156–160
Li L, Tian YP, Yang JX, Sun PP, Wu JY, Zhou HP, Zhang SY, Jin BK, Xing XJ, Wang CK, Li M, Cheng GH, Tang HH, Huang WH, Tao XT, Jiang MH. Facile synthesis and systematic investigations of a series of novel bent-shaped two-photon absorption chromophores based on pyrimidine. Chem Asian J, 2009, 4:668–680
Yanez CO, Andrade CD, Yao S, Luchita G, Bondar MV, Belfield KD. Photosensitive polymeric materials for two-photon 3D WORM optical data storage systems. J Am Chem Soc, 2009, 1:2219–2229
Zhou WH, Kuebler SM, Braun KL, Yu TY, Cammack JK, Ober CK, Perry JW, Marder SR. An efficient two-photon-generated photoacid applied to positive-tone 3D microfabrication. Science, 2002, 296:1106–1109
Kim HM, Cho BR. Two-photon probes for intracellular free metal ions, acidic vesicles, and lipid rafts in live tissues. Acc Chem Res, 2009, 42:863–872
Berezin MY, Achilefu S. Fluorescence lifetime measurements and biological imaging. Chem Rev, 2010, 110:2641–2684
Kim MK, Lim CS, Hong JT, Han JH, Jang HY, Kim HM, Cho BR. Sodium-ion-selective two-photon fluorescent probe for in vivo imaging. Angew Chem Int Ed, 2010, 49:364–367
Lee JH, Lim CS, Tian YS, Han JH, Cho BR. A two-photon fluorescent probe for thiols in live cells and tissues. J Am Chem Soc, 2010, 132:1216–1217
Wang XC, Tian XH, Zhang Q, Sun PP, Wu JY, Zhou HP, Jin BK, Yang JX, Zhang SY, Wang CK, Tao XT, Jiang MH, Tian YP. Assembly, two-photon absorption, and bioimaging of living cells of a cuprous cluster. Chem Mater, 2012, 24:954–961
Zheng Z, Yu ZP, Yang MD, Jin F, Zhang Q, Zhou Hp, Wu JY, Tian YP. Substituent group variations directing the molecular packing, electronic structure, and aggregation-induced emission property of isophorone derivatives. J Org Chem, 2013, 78:3222–3234
LaFratta CN, Fourkas JT, Baldacchini T, Farrer RA. Multiphoton fabrication. Angew Chem Int Ed, 2007, 46:6238–6258
Zhao C, Burchardt M, Brinkhoff T, Beardsley C, Simon M, Wittstock G. Microfabrication of patterns of adherent marine bacterium Phaeobacter inhibens using soft lithography and scanning probe lithography. Langmuir, 2010, 26:8641–8647
Kim S, Ohulchanskyy TY, Pudavar HE, Pandey RK, Prasad PN. Organically modified silica nanoparticles co-encapsulating photo-sensitizing drug and aggregation-enhanced two-photon absorbing fluorescent dye aggregates for two-photon photodynamic therapy. J Am Chem Soc, 2007, 129:2669–2675
Balaz M, Collins HA, Dahlstedt E, Anderson HL. Synthesis of hydrophilic conjugated porphyrin dimmers for one-photon and two-photon photodynamic therapy at NIR wavelengths. Org Biomol Chem, 2009, 7:874–888
Gallavardin T, Chloe Armagnat, Maury O, Baldeck PL, Lindgren M, Monnereau C, Andraud C. An improved singlet oxygen sensitizer with two-photon absorption and emission in the biological transparency window as a result of ground state symmetry-breaking. Chem Commun, 2012, 48:1689–1691
Abbotto A, Beverina L, Bozio R, Bradamante S, Ferrante C, Pagani GA, Signorini R. Push-pull organic chromophores for frequency up-converted lasing. Adv Mater, 2000, 12:1953–1967
Tian H, Feng YL. Next step of photochromic switches? J Mater Chem, 2008, 18: 1617–1622
Lin TC, He GS, Prasad PN, Tan LS. Degenerate nonlinear absorption and optical power limiting properties of asymmetrically substitute-dstilbenoid chromophores. J Mater Chem, 2004, 14:982–991
Li SL, Wu JY, Tian YP, Tang YW, Jiang MH, Fun HK, Chantrapromma S. Preparation, characterization, two-photon absorptio and optical limiting properties of a novel metal complex containing carbazole. Opt Mater, 2006, 28:897–903
Lin TC, Huang YJ, Chen YF, Hu CL. Two-photon absorption and effective broadband optical power limiting properties of a multi-branched chromophore containing 2,3-diarylquinoxalinyl moieties as the electron-pulling units. Tetrahedron, 2010, 66:1375–1382
Mongin O, Porrès L, Katan C, Pons T, Mertz J, Mireille B-D. Synthesis and two-photon absorption of highly soluble three-branched fluorenylene-vinylene derivatives. Tetrahedron Lett, 2003, 44:8121–8125
Grabowski ZR, Rotkiewicz K. Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures. Chem Rev, 2003, 103:3839–4031
Beverina L, Fu J, Leclercq A, Zojer E, Pacher P, Barlow S, Stryland EWV, Hagan DJ, Brédas J-L, Marder SR. Two-photon absorption at telecommunications wavelengths in a dipolar chromophore with a pyrrole auxiliary donor and thiazole auxiliary acceptor. J Am Chem Soc, 2005, 127:7282–7283
Tian YP, Li L, Zhang JZ, Yang JX, Zhou HP, Wu J, Sun PP, Tao LM, Guo YH, Wang CK, Xing H, Huang WH, Tao XT, Jiang MH. Investigations and facile synthesis of a series of novel multi-functional two-photon absorption materials. J Mater Chem, 2007, 17:3646–3654
Li L, Yang JX, Wang CX, Hu ZJ, Tian YP, Li J, Wang CK, Li M, Cheng GH, Tang HH, Huang WH, Tao XT, Jiang MH. Multi-carbazole derivatives for two-photon absorption data storage: Synthesis, optical properties and theoretical calculation. Sci Chi Chem, 2010, 53:884–890
Shao JJ, Guan ZP, Yan YL, Jiao CJ, Xu QH, Chi C. Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores. J Org Chem, 2011, 76:780–790
Liu B, Zhang Q, Ding HJ, Hu GJ, Du YJ, Wang CK, Wu JY, Li SL, Zhou HP, Yang JX, Tian YP. Synthesis, crystal structures and two-photon absorption properties of a series of terpyridine-based chromophores. Dyes Pigm, 2012, 95:149–160
Schwich T, Cifuentes MP, Gugger PA, Samoc M, Humphrey MG. Electronic, molecular weight, molecular volume, and financial cost-scaling and comparison of two-photon absorption effieciency in disparate molecules (organometallic complexes for nonlinear optics. 48.)—A response to “comment on ‘organometallic complexes for nonlinear optics. 45. Dispersion of the third-order nonlinear optical properties of triphenylamine-cored alkynylruthenium dendrimers.” Increasing the nonlinear response by two orders of magnitude.” Adv Mater, 2011, 23: 1433–1435
Roberts RL, Schwich T, Corkery TC, P.Cifuentes M, A.Green K, Farmer JD, Low PJ, Marder TB, Samoc M, Humphrey MG. Organometallic complexes for nonlinear optics. 45. Dispersion of the third-order nonlinear optical properties of triphenylamine-cored alkynylruthenium dendrimers. Adv Mater, 2009, 21: 2318–2322
Varnavski O, Yan X-Z, Mongin O, Blanchard-Desce M, Goodson T. Strongly interacting organic conjugated dendrimers with enhanced two-photon absorption. J Phys Chem C, 2007, 111:149–162
Ning ZJ, Tian H. Triarylamine: A promising core unit for efficient photovoltaic materials. Chem Commun, 2009, 45:5483–5495
Cremer J, Briehn CA. Novel highly fluorescent triphenylamine-based oligothiophenes. Chem Mater, 2007, 19:4155–4165
Sheldrick GM. SHELXTLV 5.1 software reference manual. Madison: BrukerAXS, Inc. 1997
Qiu DF, Zhao Q, Bao XY, Liu KC, Wang HW, Guo YC, Zhang LF, Zeng JL, Wang H. Electropolymerization and characterization of an alternatively conjugated donor-acceptor metallopolymer: Poly-[Ru(4′-(4-(Diphenylamino)phenyl)-2,2′:6′,2″-terpyridine)2]2+. Inorg Chem Commun, 2011, 14:296–299
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Jr. JAM, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, A.Voth G, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, D.Rabuck A, Raghavachari K, Foresman JB, Ortiz JV, Q. Cui, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian03, Revision B. 04, Wallingford: Gaussian, Inc., CT, 2004
Woo HY, Liu B, Kohler B, Korystov D, Mikhailovsky A, Bazan GC. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J Am Chem Soc, 2005, 127:14721–14729
Zheng Z, Zhang Q, Yu ZP, Yang MD, Zhou HP, Wu JY, Tian YP. Four new two-photon absorbing imidazo[4,5-f]1,10-phenanthroline derivatives dyes with different dipole moment orientation based on different group: Synthesis, optical characterization and bioimaging. J Mater Chem C, 2013, 1:822–830
Kong L, Yang JX, Zhou HP, Li SL, Hao FY, Zhang Q, Tu YL, WU J, Xue ZM, Tian YP. Synthesis, photophysical properties and TD-DFT calculation of four two-photon absorbing triphenylamine derivatives. Sci Chi Chem, 2013, 56:106–116
Hu ZJ, Zhang RL, Sun PP, Li L, Wu JY, Yang JX, Tian YP, Wang CK. Three asymmetrical conjugated D-π-D′ sulfur-containing chromophores with a focus on two-photon absorption. Aust J Chem, 2011, 64:174–179
DALTON. A molecular electronic structure program. Release Dalton. http://daltonprogram.org/.2011
Strickler JH, Webb WW. Three-dimensional optical data storage in refractive media by two-photon point excitation. Optics Letters, 1991, 16:1780–1782
Cammi R, Cossi M, Tomasi J. Analytical derivatives for molecular solutes. III. Hartree-Fock static polarizability and hyperpolarizabilities in the polarizable continuum model. J Chem Phys, 1996, 104:4611–4620
Shen YR. The Principles Of Nonlinear Optics. New York: Wiley, 1984
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Liu, J., Zhang, Q., Ding, H. et al. Two novel terpyridine-based chromophores with donor-acceptor structural model containing modified triphenylamine moiety: Synthesis, crystal structures and two-photon absorption properties. Sci. China Chem. 56, 1315–1324 (2013). https://doi.org/10.1007/s11426-013-4940-7
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DOI: https://doi.org/10.1007/s11426-013-4940-7