Abstract
The photochemistry of several photochromic arene [e]-annelated dimethyldihydropyrenes (DHPs) was studied. These compounds have much larger photochemical ring opening quantum yields than the simple DHPs, making them potentially more useful as building blocks for photoswitchable materials.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
H. Bouas-Laurent and H. Dürr, Photochromism, Molecules and Systems; Elsevier Science Publishing Co. Inc., New York, 1990.
M. Irie, Diarylethenes for Memories and Switches, Chem. Rev., 2000, 100, 1685–1716.
M. Irie, Photoswitchable Molecular Systems Based on Diarylethenes, in Molecular Photoswitches, ed. B. L. Feringa, Wiley-VCH GmbH, Weinheim, 2001, 37–61.
Y. Yokoyama, Fulgides for Memories and Switches, Chem. Rev., 2000, 100, 1717–1739.
Y. Yokoyama, Molecular Switches with Photochromic Fulgides, in Molecular Switches, ed. B. L. Feringa, Wiley-VCH GmbH, Weinheim, 2001, 107–121.
H. Bouas-Laurent and H. Dürr, Organic Photochromism (IUPAC Technical Report), Pure Appl. Chem., 2001, 73, 639–665.
J. A. Delaire and K. Nakatani, Linear and Nonlinear Optical Properties of Photochromic Molecules and Materials, Chem. Rev., 2000, 100, 1817–1845.
M. J. Marsella, Z.-Q. Wang and R. H. Mitchell, Backbone Photochromic Polymers Containing the Dimethyldihydropyrene Moiety: Toward Optoelectronic Switches, Org. Lett., 2000, 2, 2979–2982.
V. Boekelheide and J. B. Phillips, Aromatic Molecules Bearing Substituents within the Cavity of the π-Electron Cloud. Synthesis of trans-15,16-Dimethyldihydropyrene, J. Am. Chem. Soc., 1967, 89, 1695–1704.
J. B. Phillips and R. J. Molyneux and E. Sturm and V. Boekelheide, Aromatic Molecules Bearing Substituents within the Cavity of the π-Electron Cloud. Chemical Properties of trans-Dimethyldihydropyrene, J. Am. Chem. Soc., 1967, 89, 1704–1709.
R. H. Mitchell, The Metacyclophanediene-Dihydropyrene Photochromic π Switch, Eur. J. Org. Chem., 1999, 3689–2703.
R. H. Mitchell and T. R. Ward, The Synthesis of Benz-, Naphth-, and Anth-annelated Dihydropyrenes as Aids to Measuring Aromaticity by NMR, Tetrahedron, 2001, 57, 3689–3695.
R. H. Mitchell, T. R. Ward, Y. Wang and P. W. Dibble, Pi-Switches: Synthesis of Three-Way Molecular Switches Based on the Diemthyldihydropyrene-Metacyclophanediene Valence Isomerization, J. Am. Chem. Soc., 1999, 121, 2601–2602.
M. Tashiro and T. Yamato, Metacyclophanes and Related Compounds. 4. Halogenations of 8,16-Dialkyl-5,13-di-tert-butyl-[2.2]-metacyclophane-l-enes and 2,7-Di-tert-butyl-trans-10b, 10c-dihydropyrenes, J. Am. Chem. Soc., 1982, 104, 3701–3707.
T. Sawada and M. Wakabayashi and H. Takeo and A. Miyazawa and M. Tashiro and T. Thiemann and S. Mataka, Novel, Strained 10b, 10c-dihydropyrenes Bearing Bulky TMSCH2 Groups at the Internal Positions, J. Chem. Soc, Perkin Trans. 1, 1999, 403–407.
W. Schmidt, Competition Between Concerted and Non-concerted Pathways In Symmetry-Forbidden Reactions, Tetrahedron Lett., 1972, 7, 581–584.
H. R. Blattman and W. Schmidt, About the Phototropic Effects of Trans-15,16-Dimethyldihydropyrenes and their Derivatives, Tetrahedron, 1970, 26, 5885–5899.
R. S. Murphy, Y. Chen, T. R. Ward and R. H. Mitchell and C. Bohne, Photophysical Studies on the Photochromism of trans-10b, 10c-Dimethyldihydropyrene, Chem. Commun., 1999, 2097–2098.
M. A. L. Sheepwash and R. H. Mitchell and C. Bohne, Mechanistic Insights into the Photochromism of trans-10b, 10c-Dimethyl-10b, 10c-dihydropyrene Derivatives, J. Am. Chem. Soc., 2002, 124, 4693–4700.
R. S. Murphy and T. C. Barros and J. Barnes and B. Mayer, G. Marconi and C. Bohne, Complexation of Fluorenone and Xanthone to Cyclodextrins: Comparison of Theoretical and Experimental Studies, J. Phys. Chem. A, 1999, 103, 137–146.
Y. Liao and C. Bohne, Alcohol Effect on Equilibrium Constants and Dissociation Dynamics of Xanthone-Cyclodextrin Complexes, J. Phys. Chem., 1996, 100, 734–743.
D. F. Eaton, Luminescence Spectroscopy, in Handbook of Organic Photochemistry, ed. J. C. Scaiano, CRC Press, Boca Raton, 1989, vol. I, 231–239.
C. A. Parker, A New Sensitive Chemical Actinometer I. Some Trials with Potassium Ferrioxalate, Proc R Soc. London, Ser. A, 1953, 220, 104–116.
C. G. Hatchard and C. A. Parker, A New Sensitive Chemical Actinometer II. Potassium Ferrioxalate as a Standard Chemical Actinometer, Proc. R. Soc. London, Ser. A, 1956 518–536.
N. J. Bunce, Actinometry, in Handbook of Organic Photochemistry, ed. J. C. Scaiano, CRC Press, Boca Raton, 1989, vol. I, 241–259.
R. H. Mitchell and Y. Chen, Synthesis of the Elusive Dibenzannelated Dihydropyrene Dibenzo[e,1]dimethyldihydropyrene, a Molecular Photo-switch, Tetrahedron Lett., 1996, 37, 5239–5242.
See Electronic Supplementary Information for molar absorptivity coefficient values.
A. Gilbert and J. Baggott, Essentials of Molecular Photochemistry, Blackwell Scientific Publications, Oxford, 1991.
P. J. Wagner, Misleading Sigmas and Neglected Geometries: The Effects of Methyl Substitution on Rates of Triplet State Hydrogen Abstraction by the Benzoyl Group, Pure Appl. Chem., 1977, 49, 259–270.
J. P. Bays and V. Encinas and R. D. Small and J. C. Scaiano, Photochemistry of 1,5-Dirayl-1,5-diketones, J. Am. Chem. Soc., 1980, 102, 727–734.
S. L. Murov and I. Carmichael and G. L. Hug, Handbook of Photochemistry, 2nd edn, Marcel Decker, New York, 1993.
R. V. Williams and J. R. Armantrout and B. Twamley and R. H. Mitchell and T. R. Ward and S. Bandyopadhyay, A Theoretical and Experimental Scale for Aromaticity. The First Nucleus-Independent Chemical Shifts (NICS) Study of the Dimethyldihydropyrene Nucleus, J. Am. Chem. Soc., 2002, 124, 13495–13505.
A. A. Danish and M. Silverman and Y. A. Tajima, Dienophilic Reactions of Aromatic Double Bonds in the Synthesis of ß-Substituted Naphthalenes, J. Am. Chem. Soc., 1954, 76, 6144–6150.
K. Uchida and T. Matsuoka and S. Kobatake and T. Yamaguchi and M. Irie, Substituent Effect on the Photochromic Reactivity of Bis(2-thienyl)perfluorocyclopentenes, Tetrahedron, 2001, 57, 4559–4565.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sheepwash, M.A.L., Ward, T.R., Wang, Y. et al. Mechanistic studies on the photochromism of [e]-annelated dimethyldihydropyrenes. Photochem Photobiol Sci 2, 104–112 (2003). https://doi.org/10.1039/b208952a
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/b208952a