Abstract
Numerous studies of donor-acceptor conjugated linear polyenes have been carried out with the goal to understand the exact nature of the excited state electronic structure and dynamics. In this article we discuss our endeavours with regard to the excited state intramolecular charge transfer, photoisomerization and fluorescence probe properties of various donor-acceptor substituted compounds of diphenylpolyene [Ar(CH = CH) n Ar] series and ethenylindoles.
Similar content being viewed by others
References
Birge RR (1990) Nature of the primary photochemical events in rhodopsin and bacteriorhodopsin. Biochim Biophys Acta 1016:293–327
Dugave C, Demange L (2003) Cis,trans-isomerization of organic molecules and biomolecules: implications and applications. Chem Rev 103:2475–2532
Palczewski K (2006) G Protein–coupled receptor rhodopsin. Annu Rev Biochem 75:743–767
Singh AK, Hota PK (2007) Development of bacteriorhodopsin analogues and studies of charge separated excited states in the photoprocesses of linear polyenes. Photochem Photobiol 83:50–62
Alvarez R, Vaz B, Gronemeyer H, de Lera AR (2014) Functions, therapeutic applications and synthesis of retinoids and carotenoids. Chem Rev 114:1–125
Huang T-H, Hou J-Q, Kang Z-H, Wang Y-H, Lu R, Zhou H-P, Zhao X, Ma Y-G, Zhang H-Z (2013) Investigation on the linear and nonlinear optical properties of fluorenone-based linear conjugated oligomers: the influence of π-spacer. J Photochem Photobiol A Chem 261:41–45
Scarongella M, Laktionov A, Rothlisberger U, Banerji N (2013) Charge transfer relaxation in donor–acceptor type conjugated materials. J Mater Chem C 1:2308–2319
Zhang F, Jiang K-J, Huang J-H, Yu C-C, Li S-G, Chen M-G, Yang L-M, Song Y-L (2013) A novel compact DPP dye with enhanced light harvesting and charge transfer properties for highly efficient DSCs. J Mater Chem A 1:4858–4863
Wu Y, Zhu W (2013) Organic sensitizers from D-π-A to D-A-π-A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances. Chem Soc Rev 42:2039–2058
Lee JK, Jeong B-S, Kim J, Kim C, Ko J (2013) Synthesis and photochemical characterization of fumaronitrile-based organic semiconductor and its use in solution-processed small molecule organic solar cells. J Photochem Photobiol A Chem 251:25–32
Becker RS (1988) The visual process: photophysics and photoisomerization of model visual pigments and the primery reaction. Photochem Photobiol 48:369–399
Allen MT, Whitten DG (1989) The photophysics and photochemistry of α,ω-diphenyl singlet states. Chem Rev 89:1691–1702
Waldeck DH (1991) photoisomerization dynamics of stilbenes. Chem Rev 91:415–436
Gorner H, Kuhn HJ (1995) Cis,trans-photoisomerization of stilbene and stilbene like molecules. Adv Photochem 19:58–115
Arai T, Tokumaru K (1995) Present status of the photoisomerization about ethylenic bonds. Adv Photochem 20:1–57
Saltiel J, Sears DF Jr, Ko D-H, Park D-M (1995) ‘Cis,trans-isomerization of alkenes’. In: Horspool WHM, Song P-S (eds) “CRC handbook of organic photochemistry and photobiology”. CRC press, Boca Raton, pp 3–15
Singh AK, Mahalaxmi GR (2000) Photoprocesses of linearly conjugated C = C polyenes. Proc Natl Acad Sci India Sect A 70:1–26
Singh AK (2001) Excited state properties of linear polyenes: fluorescence, fluorescence probe and photoisomerization studies of donor-acceptor diarylbutadienes. J Indian Chem Soc 78:53–72
Liu RSH, Hammond GS (2003) Photochemical reactivity of polyenes: from dienes to rhodopsin, from microseconds to femtoseconds. Photochem Photobiol Sci 2:835–844
Sonoda Y, Shimoi Y, Goto M, Tohnai N, Kanesato M (2013) Fluorescence properties of (E, E, E)-1,6-di(n-naphthyl)-1,3,5-hexatriene (n = 1, 2): effects of internal rotation. J Phys Chem A 117:566–578
Das PK, Becker RS (1978) Spectroscopy of polyenes. 2. Comprehensive investigation of emission spectral properties of polyenals and polyenones related to visual chromophores. J Phys Chem 82:2093–2105
Velsko SP, Fleming GR (1982) Photochemical isomerization in solution. Photophysics of diphenylbutadiene. J Chem Phys 76:3553–3562
Shepanski JF, Keelan BW, Zewail AH (1983) Diphenylpolyene in supersonic jets: spectroscopic and picosecond dynamics. Chem Phys Lett 103:9–14
Kohler BE, Itoh T (1988) Fluorescence from the 1Bu state of diphenylhexatriene: inversion of the 11Bu and 21Ag levels in CS2. J Phys Chem 92:5120–5122
Doany FE, Heilweil EJ, Moore R, Hochstrasser RM (1984) Picosecond study of an intermediate in the trans to cis isomerization pathway of stiff-stilbene. J Chem Phys 80:201–206
Itoh T, Kohler BE (1987) Dual fluorescence of diphenylpolyenes. J Phys Chem 91:1760–1764
Saltiel J, D’Agostino J, Megarity ED, Metts L, Neuberger KR, Wrighton M, Zafirou OC (1983) In "Organic Photochemistry, Chapman OL (ed), Marcel Dekker, New York, Vol 3 pp 1–113.
Saltiel J, Waller AS, Sears DF Jr, Garrett CZ (1993) Fluorescence quantum yields of trans-stilbene-d0 and –d2 in n-hexane and n-tetradecane. Medium and deuterium isotope effects on decay processes. J Phys Chem 97:2516–2522
Saltiel J, Waller AS, Sears DF Jr, Hoburg EA, Zeglinski DM, Waldeck DH (1994) Fluorescence quantum yields and life times of substituted stilbenes in n-alkanes. A re-examination of the relationship between solute size and medium effect on the torsional relaxation. J Phys Chem 98:10689–10698
Liu RSH, Hammond GS (2005) Reflection on medium effects on photochemical reactivity. Acc Chem Res 38:396–403
Saltiel J, Krishna TSR, Laohhasurayotin K, Ren Y, Phipps K, Davis PH, Yee WA (2011) Medium effects on the direct cis,trans-photoisomerization of 1,4-diphenyl-1,3-butadiene in solution. J Phys Chem A 115:2120–2129
Saltiel J, Hutchinson SR, Chitwood K, Dmitrenko O (2012) Photoisomerization of cis-1-(3-methyl-2-naphthyl)-2-phenylethene in glassy methylcyclohexane at 77 K. J Phys Chem A 116:5293–5298
Safarzadeh-Amiri A (1986) A time-resolved fluorescence study of the dynamic Stokes’s shift of trans-4-dimethylamino-4′-cyanostilbene. Chem Phys Lett 125:272–278
Rettig W, Majenz W (1989) Competing adiabatic photoreaction channels in stilbene derivatives. Chem Phys Lett 154:335–341
Lapouyade R, Czeschka K, Majenz W, Rettig W, Gilabert E, Rulliere C (1992) Photophysics of donor-acceptor substituted stilbenes. A time-resolved fluorescence study using selectively bridged dimethylamino cyano model compounds. J Phys Chem 96:9643–9650
Gilabert E, Lapouyade R, Rulliere C (1991) Time-resolved dual fluorescence of push-pull stilbenes at high solute concentration and excitation intensity: evidence for an emitting bicimer. Chem Phys Lett 185:82–87
Rechthaler K, Kohler G (1996) Photophysical properties of a highly fluorescent push-pull stilbene. Chem Phys Lett 250:152–158
Abraham E, Oberle J, Jonusauskas G, Lapouyade R, Rulliere C (1997) Photophysics of 4-dimethylamino-4′-cyanostilbene and model compounds: dual excited states revealed by sub-picosecond transient absorption and Kerr ellipsometry. Chem Phys 214:409–423
Singh AK, Kanvah S (2000) Effect of microheterogeneous media on the fluorescence and fluorescence probe properties of donor-acceptor diarylbutadienes. New J Chem 24:639–646
Singh AK, Kanvah S (2001) Photophysical studies of substituted 1,2-diarylethenes: twisted intramolecular charge transfer fluorescence in dimethoxy cyano-substituted 1,2-diarylethene. J Chem Soc Perkin Trans 2:395–401
Pines D, Pines E, Rettig W (2003) Dual fluorescence and excited state structural relaxations in donor-acceptor stilbenes. J Phys Chem A 107:236–242
Ernsting NP, Breffke J, Vorobyev DY, Duncan DA, Pfeffer I (2008) Sub-picosecond fluorescence evolution of amino-cyano-stilbenes in methanol: polar solvation obeys continuum theory without evidence of twisting. Phys Chem Chem Phys 10:2043–2049
Johnson ID, Thomas EW, Cundall RB (1985) Fluorescence solvatochromism of nitrodiphenylhexatrienes. J Chem Soc Faraday Trans 2(81):1303–1315
Shin DM, Whitten DG (1988) Solvatochromic behavior of intramolecular charge transfer diphenylpolyenes in homogeneous solution and microheterogeneous media. J Phys Chem 92:2945–2956
Gruen H, Gorner H (1989) Trans,cis- photoisomerisation, fluorescence and relaxation phenomena of trans-4-nitro-4′-(dialkylamino) stilbenes and analogues with a nonrotatable amino group. J Phys Chem 93:7144–7152
Letard J-F, Lapouyade R, Rettig W (1993) Structure-photophysics correlations in a series of 4-(dialkylamino) stilbenes: intramolecular charge transfer in the excited state as related to the twist around the single bonds. J Am Chem Soc 115:2441–2447
Singh AK, Manjula D, Kanvah S (2000) α,ω-Diphenylpolyenes cabable of exhibiting twisted intramolecular charge transfer fluorescence: a fluorescence and fluorescence probe study of nitro- and nitrocyano-substituted 1,4- diphenylbutadienes. J Phys Chem A 104:464–471
Singh AK, Kanvah S (2001) A fluorescence emission study of nitro- and nitromethyl-substituted 1,4-diarylbutadienes in solid state. Indian J Chem 40B:965–973
Singh AK, Mahalaxmi GR (2000) Excited state properties of α,ω-diphenylpolyenes: photophysical and photochemical studies of donor-acceptor diarylbutadienes. Photochem Photobiol 71:387–396
Singh AK, Hota PK (2003) Photoreactivity of donor-acceptor ethenes. Indian J Chem 42B:2048–2053
Singh AK, Hota PK (2006) Fluorescence and photoisomerization studies of p-nitrophenyl substituted indolic ethenes. J Phys Org Chem 19:43–52
Singh AK, Asefa A (2009) Novel fluorescence emissions from 3-styrylindoles. Indian J Chem 48B:1543–1547
Asefa A, Singh AK (2010) Fluorescence emission enhancement in substituted 3-styrylindoles in the solid state. J Lumin 130:24–28
Sonoda Y, Kwok WM, Petrasek Z, Ostler R, Matousek P, Towrie M, Parker AW, Phillips D (2001) Solvent effects on the photophysical and photochemical properties of (E, E, E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene. J Chem Soc Perkin Trans 2:308–314
Gezawy HE, Rettig W, Lapouyade R (2005) Model studies of spectral and photophysical characteristics of donor-acceptor-polyenes: dimethylamino-cyano-diphenylbutadiene. Chem Phys Lett 401:140–148
Rafiq S, Sen P (2013) Dielectric controlled excited state relaxation pathways of a representative push-pull stilbene: a mechanistic study using femtosecond fluorescence up-conversion technique. J Chem Phys 138:84308–84310
Lin C-K, Wang Y-F Y-F, Cheng Y-C, Yang J-S (2013) Multisite constrained model of trans-4-(N, N-dimethylamino)-4-nitrostilbene for structural elucidation of radiative and nonradiative excited state. J Phys Chem A 117:3158–3164
Waddell WH, Chihara K (1981) Activation barriers for the trans,cis- photoisomerization of all-trans-retinal. J Am Chem Soc 103:7389–7390
Ramamurthy V, Denny M, Liu RSH (1981) Photoisomerization of the C15- aldehyde and the C18-ketone in the vitamin A series. Solvent effect on photoisomerization of compounds related to retinal. Tetrahedron Lett 22:2463–2466
Mooney WF III, Brown PE, Russell JC, Costa SB, Pedersen LG, Whitten DG (1984) Photochemical reactions in organised assemblies. 37. Photochemistry and photophysics of surfactant trans-stilbene in supported multilayers and films at the air-water interface. J Am Chem Soc 106:5659–5667
Suddaby B, Brown PE, Russell JC, Whitten DG (1985) Photochemical reactions in organised assemblies.44. Surfactant and hydrophobic derivatives of trans-stilbenes as probes of vesicle and micelle solubilisation sites. Studies using fluorescence and photoisomerization as probes. J Am Chem Soc 107:5609–5617
Görner H (1987) The cis-trans isomerization of nitrostilbenes XV: mixed singlet and triplet mechanism for trans-cis photoisomerization of 4-nitro-4′-dialkylamino stilbenes in non-polar solvents. J Photochem Photobiol A 40:325–329
Devel P, Singh AK (1988) Photoisomerization of all-trans-retinal in organic solvents and organised media. J Photochem Photobiol A Chem 42:329–336
Arjunan P, Liu RSH (1988) Regioselective photoisomerization of pentaenals. Effect of methyl substituents. Tetrahedron Lett 29:853–856
Kim SK, Courtney SH, Fleming GR (1989) Isomerization of t-stilbene in alcohol. Chem Phys Lett 159:543–548
Lewis FD, Kalgutkar RS, Yang J-S (1999) The photochemistry of trans-ortho-, −meta-, and –para-aminostilbenes. J Am Chem Soc 121:12045–12053
Gurzadyan G, Görner H (2000) Picosecond transient absorption spectroscopy of trans-4-R-4′-nitrostilbenes with R: OMe, NH2 and NMe2. Chem Phys Lett 319:164–172
Yang J-S, Chiou S-Y, Liau K-L (2002) Fluorescence enhancement of trans-4-aminostilbene by N-phenyl substitutions: “the amino conjugation effect”. J Am Chem Soc 124:2518–2527
Papper V, Pines D, Likhtenshtein G, Pines E (1997) Photophysical characterization of trans-4,4′- disubstituted stilbenes. J Photochem Photobiol A Chem 111:87–96
Papper V, Likhtenshtein GI (2001) Substituted stilbenes: A new view on well-known systems. New applications in chemistry and biophysics. J Photochem Photobiol A Chem 140:39–52
Seydack M, Bendig J (2001) The anomalous excited state temperature behaviour of trans-4,4′-diaminostilbene and trans-4,4′-di(phenyl-ureanyl)-stilbene. J Phys Chem A 105:5731–5733
Cordes T, Schadendorf T, Priewisch B, Ruck-Braun K, Zinth W (2008) The Hammett relationship and reactions in the excited electronic state: Hemithioindigo Z/E photoisomerization. J Phys Chem A 112:581–588
Yang J-S, Lin C-K, Lahoti AM, Tseng C-K, Liu Y-H, Lee G-H, Peng S-M (2009) Effect of ground state twisting on the trans-cis photoisomerization and TICT state formation of amino stilbenes. J Phys Chem A 113:4868–4877
Wulfman CE, Kumei S (1971) Highly polarizable singlet excited states of alkenes. Science 172:1061–1061
Mathies R, Stryer L (1976) Retinal has a highly dipolar vertically excited singlet state: implications for vision. Proc Natl Acad Sci U S A 73:2169–2173
Salem L (1979) The sudden polarization effect and its possible role in vision. Acc Chem Res 12:87–92
Bonacic-Koutecky V, Koutecky J, Michl J (1987) Neutral and charged biradicals, zwitterions, funnels in S1 and proton translocation: their role in photochemistry, photophysics and vision. Angew Chem Int Ed 26:170–189
Viel A, Krawczyk RP, Manthe U, Domcke W (2003) The sudden-polarisztion effect and its role in the ultrafast photochemistry of ethene. Angew Chem Int Ed 42:3434–3436
Warshel A (1976) Bicycle-pedal model for the first step in the vision process. Nature (New Biol) 260:679–683
Saltiel J, Krishna TSR, Lachhasurayotin S, Fort K, Clark RJ (2008) Photoisomerization of cis, cis to trans, trans-1,4-diaryl-1,3-butadienes in the solid state: the Bicycle-Pedal Mechanism. J Phys Chem A 112:199–209
Liu RSH, Hammond GS (2000) The case of medium dependent dual mechanisms for photoisomerization: one-bond-flip and Hula-twist. Proc Natl Acad Sci U S A 97:11153–11158
Imamoto Y, Kuroda T, Kataoka M, Shevyakov S, Krishnamoorthy G, Liu RSH (2003) Photoisomerization by Hula-twist: 2, 2′-dimethylstilbene and a ring-fused analogue. Angew Chem Int Ed 42:3630–3633
Saltiel J, Bremer MA, Lachhasurayotin S, Krishna TSR (2008) Photoisomerization of cis, cis and cis, trans-1,4-di-o-tolyl-1,3-butadiene in glassy media at 77 K: one-bond-twist and bicycle-pedal mechanisms. Angew Chem Int Ed 47:1237–1240
Nakanishi K, B-Nair V, Arnaboldi M, Tsujimoto K, Honig B (1980) An external point charge model for bacteriorhodopsin to account for its purple colour. J Am Chem Soc 102:7945–7947
Kakitani H, Kakituni T, Rodman H, Honig B (1985) On the mechanism of wavelength regulation in visual pigments. Photochem Photobiol 41:471–479
Sakmar TP, Franke RR, Khorana HB (1991) The role of the retinylidene Schiff base counterion in rhodopsin in determining wavelength absorbance and Schiff base pKa. Proc Natl Acad Sci U S A 88:3079–3083
Yan B, Spudich JL, Mazur P, Vunnam S, Derguini F, Nakanishi K (1995) Spectral tuning in bacteriorhodopsin in the absence of counterion and coplanarisation effects. J Biol Chem 270:29668–29670
Takahashi Y, Ebrey TG (2003) Molecular basis of spectral tuning in the newt short wavelength sensitive visual pigment. Biochemistry 42:6025–6034
Sczepan M, Rettig W, Tolmachev AI (2003) Spectral and photophysical characteristics of unsymmetric polymethine dyes as model compounds for the colour shift of visual pigments. Photochem Photobiol Sci 2:1264–1271
Ogren JI, Mamaev S, Russano D, Li H, Spudich JL, Rothschild KJ (2014) Retinal chromophore structure and Schiff base interactions in red-shifted channel rhodopsin-1 from Chlamydomonas augustae. Biochemistry 53:3961–3970
Singh AK, Darshi M (2003) Bacteriorhodopsin analogs from diphenylpolyene chromophores. Photochem Photobiol 78:503–510
Hota PK, Singh AK (2007) Bacteriorhodopsin analogue from indolic chromophores. Lett Org Chem 4:300–305
Marty A, Boiret M, Deumie M (1986) How to illustrate ligand-protein binding in a class experiment. An elementary fluorescent assay. J Chem Edu 63:365–366
Davis DM, Birch DJS (1996) Extrinsic fluorescence probe study of human serum albumin using nile red. J Fluoresc 6:23–32
Plasek J, Sigler K (1996) Slow fluorescent indicators of membrane potential: a survey of different approaches to probe response analysis. J Photochem Photobiol B Biol 33:101–124
Sohi JL, Splittgerber AG (1991) The binding of coomassie brilliant blue to bovine serum albumin. A physical biochemistry experiment. J Chem Edu 68:262–264
Nakamaru Y, Sato C (2000) Identical independent sites for dye ligand on bovine serum albumin demonstrated by multivariate analysis. Biochim Biophys Acta 1480:321–328
Lunardi CN, Tedesco AC, Kurth TL, Brinn IM (2003) The complex between 9-(n-decanyl)acridone and Bovine Serum Albumin. Part 2. What do fluorescence probes probe? Photochem Photobiol Sci 2:954–959
Jun H, Hong SY, Yoon SS, Kang C, Suh M (2004) Fluorescent hydrophobic probes based on intramolecular charge transfer state for sensitive protein detection in solution. Chem Lett 33:690–691
Singh AK, Darshi M (2004) A fluorescence study of (4-{(1E, 3E)-4-[4(dimethylamino)phenyl]-buta-1,3-dienyl}phenyl)methanol and its bioconjugates with bovine and human serum albumins. New J Chem 28:120–126
Singh AK, Darshi M (2002) Fluorescence probe properties of intramolecular charge transfer diphenylbutadienes in micelle and vesicles. Biochim Biophys Acta 1563:35–44
Singh AK, Hota PK (2007) Ethenylindoles as neutral hydrophobic fluorescence probes. J Phys Org Chem 20:624–629
Singh AK, Asefa A (2009) A fluorescence study of differently substituted 3-styrylindoles and their interaction with bovine serum albumin. Luminscence 24:123–230
Asefa A, Singh AK (2009) A fluorescence study of novel styrylindoles in homogeneous and microheterogeneous media. J Fluoresc 19:921–930
Weber G, Farris FJ (1979) Synthesis and spectral properties of a hydrophobic fluorescent probe: 6- Propionyl-2-(dimethylamino) naphthalene. Biochemistry 18:3075–3078
Acknowledgments
We gratefully acknowledge contributions of our group members whose works are cited in this article. We thank the reviewers and the Editor for their valuable comments and suggestion.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hota, P.K., Singh, A.K. Donor-Acceptor Conjugated Linear Polyenes: A Study of Excited State Intramolecular Charge Transfer, Photoisomerization and Fluorescence Probe Properties. J Fluoresc 28, 21–28 (2018). https://doi.org/10.1007/s10895-014-1430-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-014-1430-z