Abstract
A series of new asymmetric chromophores containing aromatic substituents and possessing the excellent π-extension in space were prepared through multi-steps routes. One-photon and two-photon spectral properties of these new chromophores could be tuned by these substituents finely and simultaneously. The linear correlation of the wave numbers of the one-photon absorption and emission maxima to Hammett parameters of these substituents was presented. Near infrared two-photon absorption emission integrated areas of the target chromophores were correlated linearly to Hammett constants of these substituted groups.
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
Kreisel D, Nava RG, Li W, Zinselmeyer BH, Wang B, Lai J, Pless R, Gelman AE, Krupnick AS, Miller MJ (2010) In vivo two-photon imaging reveals monocyte-dependent neutrophil extravasation during pulmonary inflammation. Proc Natl Acad Sci U S A 107(42):18073–18078
Belfield KD, Schafer KJ (2002) A new photosensitive polymeric material for WORM optical data storage using multichannel two-photon fluorescence readout. Chem Mater 14(9):3656–3662
Nguyen LH, Straub M, Gu M (2005) Acrylate-based photopolymer for two-photon microfabrication and photonic applications. Adv Funct Mater 15(2):209–216
Kim HM, Jeong MY, Ahn HC, Jeon SJ, Cho BR (2004) Two-photon sensor for metal ions derived from azacrown ether. J Org Chem 69(17):5749–5751
Liu ZQ, Shi M, Li FY, Fang Q, Chen ZH, Yi T, Huang CH (2005) Highly selective two-photon chemosensors for fluoride derived from organic boranes. Org Lett 7(24):5481–5484
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
Gary-Bobo M, Mir Y, Rouxel C, Brevet D, Basile I, Maynadier M, Vaillant O, Mongin O, Blanchard-Desce M, Morère A, Garcia M, Durand J-O, Raehm L (2011) Mannose-functionalized mesoporous silica nanoparticles for efficient two-photon photodynamic therapy of solid tumors. Angew Chem Int Ed 50(49):11425–11631
Lee SK, Yang WJ, Choi JJ, Kim CH, Joen SJ, Cho BR (2005) 2,6-Bis[4-(p-dihexylaminostyryl)styryl]anthracene derivatives with large two-photon cross sections. Org Lett 7(2):323–326
Strehmel B, Sarker AM, Detert H (2003) The influence of σ and π acceptors on two-photon absorption and solvatochromism of dipolar and quadrupolar unsaturated organic compounds. Chem Phy Chem 4(3):249–259
Rogers CJ, Dickerson TJ, Brogan AP, Janda KD (2005) Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis. J Org Chem 70(9):3705–3708
Brink BD, DeFrancisco JR, Hillner JA, Linton BR (2011) Curtin–hammett and steric effects in HOBt acylation regiochemistry. J Org Chem 76(13):5258–5263
Antonov L, Kamada K, Ohta K, Kamounah FS (2003) A systematic femtosecond study on the two-photon absorbing D-π-A molecules–π-bridge nitrogen insertion and strength of the donor and acceptor groups. Phys Chem Chem Phys 5:1193–1197
Drobizhev M, Makarov NS, Stepanenko Y, Rebane A (2006) Near-infrared two-photon absorption in phthalocyanines: enhancement of lowest gerade-gerade transition by symmetrical electron-accepting substitution. J Chem Phys 124:224701
Li JY, Li Q, Liu D (2011) Novel Thieno-[3,4-b]-Pyrazines cored dendrimers with carbazole dendrons: design, synthesis, and application in solution-processed red organic light-emitting diodes. ACS Appl Mater Int 3(6):2099–2107
Huang LT, Yen HJ, Liou GS (2011) Substituent effect on electrochemical and electrochromic behaviors of ambipolar aromatic polyimides based on aniline derivatives. Macromolecules 44(24):9595–9610
Perrin D, Armarego W, Perrin D (1966) Purification of laboratory chemicals. Pergamon, New York
Fischer M, Georges J (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, Rettig W (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
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
Zgiershi MZ, Grabowska A (2000) Photochromism of Salicylideneaniline (SA). How the photochromic transient is created: a theoretical approach. J Chem Phys 12(14):6329–6338
Yi PG, Liang YH, Cao CZ (2005) Intramolecular proton or hydrogen-atom transfer in the ground and excited-states of 2-hydroxybenzophenone: a theoretical study. Chem Phys 315(3):297–302
Liang YH, Yi PG (2007) Theoretical studies on structure, energetic and intramolecular proton transfer of Alkannin. Chem Phys Lett 438(4–6):173–177
Yang ZN, Yang SY, Zhang JP (2007) Ground-and excited-state proton transfer and rotamerism in 2-(2-Hydroxyphenyl)-5-Phenyl-1, 3, 4-Oxadiazole and its O/“NH or S”-substituted derivatives. J Phys Chem A 111(28):6354–6360
Iyoda M, Nakamura N, Todaka M, Ohtsu S, Hara K, Kuwatani Y, Yoshida M, Matsuyama H, Sugita M, Tachibana H, Inoue H (2000) Novel synthesis of hexaaryl[3]radialenes via dibromo[3]dendralenes. Tetrahedron Lett 41(36):7059–7064
Hansch C, Leo A, Taft RW (1991) A survey of Hammett substituent constants and resonance and field parameters. Chem Rev 91(2):165–195
Lippert E (1957) Spektroskopische Bistimmung Des Dipolmomentes Aromatischer Verbindungen im Ersten Angeregten Singulettzustand. Z Electrochem 61:962
Kim S, Zheng QD, He GS, Bharali DJ, Pudavar HE, Baev A, Prasad PN (2006) Aggregation-enhanced fluorescence and two-photon absorption in nanoaggregates of a 9,10-Bis[4′-(4″-aminostyryl)styryl]anthracene derivative. Adv Funct Mater 16(18):2317–2323
Wan Y, Jia K, Li BS, Bo ZS, Xia AD (2006) Enhancement of two-photon absorption cross-section and singlet-oxygen generation in porphyrins upon β-functionalization with donor − acceptor substituents. Org Lett 8(13):2719–2722
Lee EC, Hong BH, Lee JY, Kim JC, Kim D, Kim Y, Kim KS (2005) Substituent effects on the edge-to-face aromatic interactions. J Am Chem Soc 127(12):4530–4537
Qian Y, Li S, Zhang G, Wang Q, Wang S, Xu H, Yang G (2007) Aggregation-induced emission enhancement of 2-(2′-hydroxyphenyl) benzothiazole-based excited-state intramolecular proton-transfer compounds. J Phys Chem B 111(21):5861–5868
Acknowledgments
This work was finically supported by chongqing natural science foundation projects CSTC2012JJB50007 and CSTC2010BB0216. H. Li is grateful to the Postdoctoral Science Foundation of China for their encouraging supporting (Grants 22012T50762 & 2011M501388). We greatly appreciate Key Laboratory of Photochemical Conversion and Optoelectronic Materials, CAS for the help in the laser detection.
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The supplementary materials including the Figures S1~S5, Table S1 as well as the synthesis of the molecules association with this work are available at the website of the journal. (DOC 4663 kb)
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Hu, N., Gong, Y., Wang, X. et al. A Successful Attempt to Obtain the Linear Dependence Between One-Photon and Two-Photon Spectral Properties and Hammett Parameters of Various Aromatic Substituents in New π-Extended Asymmetric Organic Chromophores. J Fluoresc 25, 1559–1566 (2015). https://doi.org/10.1007/s10895-015-1637-7
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DOI: https://doi.org/10.1007/s10895-015-1637-7