4 Stepwise Two-Photon Photochromism
77
25. Kobayashi Y, Abe J (2016) Real-time dynamic hologram of a 3D object with fast photochromic
molecules. Adv Opt Mater 4:1354–1357
26. Mutoh K, Nakano E, Abe J (2012) Spectroelectrochemistry of a photochromic
[2.2]paracyclophane-bridged imidazole dimer: clarification of the electrochemical behavior
of HABI. J Phys Chem A 116:6792–6797
27. Uno T, Koga M, Sotome H, Miyasaka H, Tamai N, Kobayashi Y (2018) Stepwise twophoton-induced electron transfer from higher excited states of noncovalently bound porphyrinCdS/ZnS core/shell nanocrystals. J Phys Chem Lett 9:7098–7104
28. Kobayashi Y, Mutoh K, Abe J (2016) Fast photochromic molecules toward realization of
photosynergetic effects. J Phys Chem Lett 7:3666–3675
29. Fihey A, Perrier A, Browne WR, Jacquemin D (2015) Multiphotochromic molecular systems.
Chem Soc Rev 44:3719–3759
30. Mutoh K, Nakagawa Y, Sakamoto A, Kobayashi Y, Abe J (2015) Stepwise two-photon-gated
photochemical reaction in photochromic [2.2]paracyclophane-bridged bis(imidazole dimer). J
Am Chem Soc 137:5674–5677
31. Mayer U, Baumgartel H, Zimmermann H (1966) Über biradikale, chinone und semichinone
der imidazolyl-reihe. Angew Chem 78:303
32. Kikuchi A, Iwahori F, Abe J (2004) Definitive evidence for the contribution of biradical character in a closed-shell molecule, derivative of 1,4-bis-(4,5-diphenylimidazol-2ylidene)cyclohexa-2,5-diene. J Am Chem Soc 126:6526–6527
33. Yamashita H, Abe J (2014) Pentaarylbiimidazole, PABI: an easily synthesized fast
photochromic molecule with superior durability. Chem Commun 50:8468–8471
34. Yamashita H, Ikezawa T, Kobayashi Y, Abe J (2015) Photochromic phenoxyl-imidazolyl radical
complexes with decoloration rates from tens of nanoseconds to seconds. J Am Chem Soc
137:4952–4955
35. Ikezawa T, Mutoh K, Kobayashi Y, Abe J (2016) Thiophene-substituted phenoxyl-imidazolyl
radical complexes with high photosensitivity. Chem Commun 52:2465–2468
36. Mutoh K, Kobayashi Y, Yamane T, Ikezawa T, Abe J (2017) Rate-tunable stepwise two-photongated photoresponsive systems employing a synergetic interaction between transient biradical
units. J Am Chem Soc 139:4452–4461
37. Siewertsen R, Neumann H, Buchheim-stehn B, Herges R, Näther C, Renth F, Temps F (2009)
Highly efficient reversible Z−E photoisomerization of a bridged azobenzene with visible light
through resolved S 1 (nπ*) absorption bands. J Am Chem Soc 131:15594–15595
38. Beharry AA, Sadovski O, Woolley GA (2011) Azobenzene photoswitching without ultraviolet
light. J Am Chem Soc 133:19684–19687
39. Bléger D, Schwarz J, Brouwer AM, Hecht S (2012) o-Fluoroazobenzenes as readily synthesized
photoswitches offering nearly quantitative two-way isomerization with visible light. J Am
Chem Soc 134:20597–20600
40. Fukaminato T, Hirose T, Doi T, Hazama M, Matsuda K, Irie M (2014) Molecular design strategy
toward diarylethenes that photoswitch with visible Light. J Am Chem Soc 136:17145–17154
41. Bléger D, Hecht S (2015) Visible-light-activated molecular switches. Angew Chem Int Ed
54:11338–11349
42. Petermayer C, Dube H (2018) Indigoid photoswitches: visible light responsive molecular tools.
Acc Chem Res 51:1153–1163
43. Hemmer JR, Page ZA, Clark KD, Stricker F, Dolinski ND, Hawker CJ, Read De Alaniz J (2018)
Controlling dark equilibria and enhancing donor-acceptor stenhouse adduct photoswitching
properties through carbon acid design. J Am Chem Soc 140:10425–10429
44. Bochet CG (2000) Wavelength-selective cleavage of photolabile protecting groups. Tetrahedron
Lett 41:6341–6346
45. Lerch MM, Hansen MJ, Velema WA, Szymanski W, Feringa BL (2016) Orthogonal photoswitching in a multifunctional molecular system. Nat Commun 7:12054
46. Ashkenasy G, Hermans TM, Otto S, Taylor AF (2017) Systems chemistry. Chem Soc Rev
46:2543–2554
77
25. Kobayashi Y, Abe J (2016) Real-time dynamic hologram of a 3D object with fast photochromic
molecules. Adv Opt Mater 4:1354–1357
26. Mutoh K, Nakano E, Abe J (2012) Spectroelectrochemistry of a photochromic
[2.2]paracyclophane-bridged imidazole dimer: clarification of the electrochemical behavior
of HABI. J Phys Chem A 116:6792–6797
27. Uno T, Koga M, Sotome H, Miyasaka H, Tamai N, Kobayashi Y (2018) Stepwise twophoton-induced electron transfer from higher excited states of noncovalently bound porphyrinCdS/ZnS core/shell nanocrystals. J Phys Chem Lett 9:7098–7104
28. Kobayashi Y, Mutoh K, Abe J (2016) Fast photochromic molecules toward realization of
photosynergetic effects. J Phys Chem Lett 7:3666–3675
29. Fihey A, Perrier A, Browne WR, Jacquemin D (2015) Multiphotochromic molecular systems.
Chem Soc Rev 44:3719–3759
30. Mutoh K, Nakagawa Y, Sakamoto A, Kobayashi Y, Abe J (2015) Stepwise two-photon-gated
photochemical reaction in photochromic [2.2]paracyclophane-bridged bis(imidazole dimer). J
Am Chem Soc 137:5674–5677
31. Mayer U, Baumgartel H, Zimmermann H (1966) Über biradikale, chinone und semichinone
der imidazolyl-reihe. Angew Chem 78:303
32. Kikuchi A, Iwahori F, Abe J (2004) Definitive evidence for the contribution of biradical character in a closed-shell molecule, derivative of 1,4-bis-(4,5-diphenylimidazol-2ylidene)cyclohexa-2,5-diene. J Am Chem Soc 126:6526–6527
33. Yamashita H, Abe J (2014) Pentaarylbiimidazole, PABI: an easily synthesized fast
photochromic molecule with superior durability. Chem Commun 50:8468–8471
34. Yamashita H, Ikezawa T, Kobayashi Y, Abe J (2015) Photochromic phenoxyl-imidazolyl radical
complexes with decoloration rates from tens of nanoseconds to seconds. J Am Chem Soc
137:4952–4955
35. Ikezawa T, Mutoh K, Kobayashi Y, Abe J (2016) Thiophene-substituted phenoxyl-imidazolyl
radical complexes with high photosensitivity. Chem Commun 52:2465–2468
36. Mutoh K, Kobayashi Y, Yamane T, Ikezawa T, Abe J (2017) Rate-tunable stepwise two-photongated photoresponsive systems employing a synergetic interaction between transient biradical
units. J Am Chem Soc 139:4452–4461
37. Siewertsen R, Neumann H, Buchheim-stehn B, Herges R, Näther C, Renth F, Temps F (2009)
Highly efficient reversible Z−E photoisomerization of a bridged azobenzene with visible light
through resolved S 1 (nπ*) absorption bands. J Am Chem Soc 131:15594–15595
38. Beharry AA, Sadovski O, Woolley GA (2011) Azobenzene photoswitching without ultraviolet
light. J Am Chem Soc 133:19684–19687
39. Bléger D, Schwarz J, Brouwer AM, Hecht S (2012) o-Fluoroazobenzenes as readily synthesized
photoswitches offering nearly quantitative two-way isomerization with visible light. J Am
Chem Soc 134:20597–20600
40. Fukaminato T, Hirose T, Doi T, Hazama M, Matsuda K, Irie M (2014) Molecular design strategy
toward diarylethenes that photoswitch with visible Light. J Am Chem Soc 136:17145–17154
41. Bléger D, Hecht S (2015) Visible-light-activated molecular switches. Angew Chem Int Ed
54:11338–11349
42. Petermayer C, Dube H (2018) Indigoid photoswitches: visible light responsive molecular tools.
Acc Chem Res 51:1153–1163
43. Hemmer JR, Page ZA, Clark KD, Stricker F, Dolinski ND, Hawker CJ, Read De Alaniz J (2018)
Controlling dark equilibria and enhancing donor-acceptor stenhouse adduct photoswitching
properties through carbon acid design. J Am Chem Soc 140:10425–10429
44. Bochet CG (2000) Wavelength-selective cleavage of photolabile protecting groups. Tetrahedron
Lett 41:6341–6346
45. Lerch MM, Hansen MJ, Velema WA, Szymanski W, Feringa BL (2016) Orthogonal photoswitching in a multifunctional molecular system. Nat Commun 7:12054
46. Ashkenasy G, Hermans TM, Otto S, Taylor AF (2017) Systems chemistry. Chem Soc Rev
46:2543–2554