Synthesis and photochromic properties of symmetrical aryl ether linked bi- and tri-naphthopyrans

Gabbutt, Christopher D.; Heron, B. Mark; Instone, Alicia C.; Kolla, Suresh B.; Mahajan, Kunal; Coelho, Paulo J.; Carvalho, Luís M.

doi:10.1016/j.dyepig.2006.07.028

Cited by 12 publications

(9 citation statements)

References 20 publications

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“…The TC forms are more thermally labile than the TT ones, whilst their thermodynamic stability is generally higher than that of TT. 9,10 This behaviour has also been observed for the reference molecule having this skeleton, 3,3diphenyl-3H-naphtho [2,1-b]pyran (herein named RN, Scheme 1), that was extensively reported in the literature, especially over the last three decades. 5,7,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] The transformation of a benzo-or a naphthopyran into a photochromic system possessing only a T-Type or a P-Type behaviour might undoubtedly be of interest from both points of view of basic research and practical applications.…”

Section: Introductionsupporting

confidence: 61%

Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Frigoli

Jousselin‐Oba

Mamada

et al. 2020

Photochem Photobiol Sci

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Section: Introductionsupporting

confidence: 61%

Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Frigoli

Jousselin‐Oba

Mamada

et al. 2020

Photochem Photobiol Sci

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“…[46] For RC,t he TC form is less thermally stable by about three to four orders of magnitude compared with TT,a nd its thermodynamic stability is higher than that of TT (Scheme 1). [47] To reach ah igh thermalp ersistence of colour generated upon UV irradiation and consequently to obtain Twon ovel helical naphthopyrans have been synthesised.T he helical scaffold has the interesting effect of increasing the thermal stability of the transoid-trans (TT) open isomer formed upon UV irradiationo ft he closed form (CF), which transforms these naphthopyrans from thermal to photochemical photochromes. The photochromic performance is excellent in both polar and apolar solvents and the conversion percentagef rom the CF to the TT form can be as high as 92.8 %.…”

Section: Introductionmentioning

confidence: 99%

P‐Type Photochromism of New Helical Naphthopyrans: Synthesis and Photochemical, Photophysical and Theoretical Study

et al. 2015

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Two novel helical naphthopyrans have been synthesised. The helical scaffold has the interesting effect of increasing the thermal stability of the transoid-trans (TT) open isomer formed upon UV irradiation of the closed form (CF), which transforms these naphthopyrans from thermal to photochemical photochromes. The photochromic performance is excellent in both polar and apolar solvents and the conversion percentage from the CF to the TT form can be as high as 92.8 %. We propose a new method to determine the quantum yields of the photochemical processes that lead to transoid-cis (TC) and TT isomers, and their molar absorption coefficients. The thermal stability of the TT and TC isomers has been studied in different solvents. The quantum yields of fluorescence before and after irradiation, along with the decay lifetimes, have also been measured. TD-DFT calculations have been performed to determine the relative thermodynamic stability of the species involved in the photochromic mechanism and to rationalise their spectral properties.

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“…The classical behavior of these molecules, where the UV irradiation of the closed form leads to photoproduction of the transoid‐cis (TC) and transoid‐trans (TT) structures, can be exemplified by the 3,3‐diphenyl‐[3H]‐naphtho[2–1b]pyran . The TC is generally more thermally labile compared to TT while its thermodynamic stability is usually higher than that of TT .…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of helical chromenes with chloromethyl phenylcarbamate polysaccharide‐based stationary phases

Ianni

Scorzoni

Gentili

et al. 2018

J of Separation Science

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Two chloromethyl phenylcarbamate-based chiral stationary phases, one containing an amylose-type chiral selector (Lux Amylose 2, from Phenomenex) and the other a cellulose-type one (Lux Cellulose-4, from Phenomenex), were successfully used for the chiral resolution of three helical chromenes featuring a helicene-like structure. The compound bearing a phenyl substituent on the helicene-like structure was enantioresolved at 25°C with Lux Cellulose-4 and a n-hexane/1-propanol 99:1 v/v eluent. With a n-hexane/2-propanol 99.8:0.2 v/v mobile phase, the same column (operated at 35°C) provided the separation of the four isomers of the compound having a hexyl residue on the helicene-like motif and an additional asymmetric carbon. Lux Amylose-2 was necessary for the enantioseparation of the compound having the sole hexyl residue on the helical scaffold. For the last compound a n-hexane/2-propanol 99.8:0.2 v/v eluent was used, and the column temperature was fixed at 5°C. The enantiomer elution order was appraised by using electronic circular dichroism and theoretical calculations. Notably, different thermodynamics of retention and enantioseparation were observed for molecules with pronounced structural similarity, that is, the enantiomer pairs of the compound containing the additional asymmetric carbon atom. Indeed, both entropically and enthalpically controlled adsorption and separation processes were observed.

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Synthesis and photochromic properties of symmetrical aryl ether linked bi- and tri-naphthopyrans

Cited by 12 publications

References 20 publications

Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

P‐Type Photochromism of New Helical Naphthopyrans: Synthesis and Photochemical, Photophysical and Theoretical Study

Chiral separation of helical chromenes with chloromethyl phenylcarbamate polysaccharide‐based stationary phases

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