80
2 Biphenyl Moiety for a Solvent Responsive Aryl Gold(I) …
10. (a) Sagara Y, Mutai T, Yoshikawa I, Araki K (2007) Material design for piezochromic luminescence: hydrogen-bond-directed assemblies of a pyrene derivative. J Am Chem Soc 129:1520–
1521. (b) Ooyama Y, Kagawa Y, Fukuoka H, Ito G, Harima Y (2009) Mechanofluorochromism
of a series of benzofuro[2,3-c]oxazolo[4,5-a]carbazole-type fluorescent dyes. Eur J Org Chem
2009:5321–5326. (c) Yoon S-J, Chung JW, Gierschner J, Kim KS, Choi M-G, Kim D, Park
SY (2010) Multistimuli two-color luminescence switching via different slip-stacking of highly
fluorescent molecular sheets. J Am Chem Soc 132:13675–13683. (d) Zhang G, Lu J, Sabat
M, Fraser CL (2010) Polymorphism and reversible mechanochromic luminescence for solidstate difluoroboron avobenzone. J Am Chem Soc 132:2160–2162. (e) Sagara Y, Kato T (2011)
Brightly tricolored mechanochromic luminescence from a single-luminophore liquid crystal:
reversible writing and erasing of images. Angew Chem Int Ed 50:9128–9132. (f) Mizoshita N,
Tani T, Inagaki S (2012) Isothermally reversible fluorescence switching of a mechanochromic
perylene bisimide dye. Adv Mater 24:3350–3355. (g) Nagura K, Saito S, Yusa H, Yamawaki H,
Fujihisa H, Sato H, Shimoikeda Y, Yamaguchi S (2013) Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chromism of tetrathiazolylthiophene. J Am Chem
Soc 135:10322–10325. (h) Yagai S, Okamura S, Nakano Y, Yamauchi M, Kishikawa K, Karatsu
T, Kitamura A, Ueno A, Kuzuhara D, Yamada H, Seki T, Ito H (2014) Design amphiphilic
dipolar π-systems for stimuli-responsive luminescent materials using metastable states. Nat
Commun 5:4013. (i) Sagara Y, Lavrenova A, Crochet A, Simon Y C, Fromm K M, Weder
C (2016) A Thermo- and mechanoresponsive cyano-substituted oligo(p-phenylene vinylene)
derivative with five emissive states. Chem Eur J 22:4374–4378
11. Seki T, Ozaki T, Okura T, Asakura K, Sakon A, Uekusa H, Ito H (2015) Interconvertible
Multiple Photoluminescence Color of a Gold(I) Isocyanide Complex in the Solid State: SolventInduced Blue-Shifted and Mechano-Responsive Red-Shifted Photoluminescence. Chem Sci 6:
2187–2195
12. (a) Seki T, Sakurada K, Ito H (2013) Controlling mechano- and seeding-triggered singlecrystalto-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds.
Angew Chem Int Ed 52:12828–12832. (b) Ito H, Muromoto M, Kurenuma S, Ishizaka S,
Kitamura N, Sato H, Seki T (2013) Mechanical stimulation and solid seeding trigger singlecrystal-to-single-crystal molecular domino transformations. Nat Commun 4:2009. (c) Seki
T, Sakurada K, Ito H (2015) Mismatched changes of the photoluminescence and crystalline
structure of a mechanochromic gold(i) isocyanide complex. Chem Commun 51:13933–13936.
(d) Yagai S, Seki T, Aonuma H, Kawaguchi K, Karatsu T, Okura T, Sakon A, Uekusa H, Ito H
(2016) Mechanochromic luminescence based on crystal-to-crystal transformation mediated by
a transient amorphous state. Chem Mater 28:234–241. (e) Seki T, Takamatsu Y, Ito H (2016) A
screening approach for the discovery of mechanochromic gold(i) isocyanide complexes with
crystal-to-crystal phase transitions. J Am Chem Soc 138:6252–6260
13. Seki T, Sakurada K, Muromoto M, Ito H (2015) Photoinduced single-crystal-to-single-crystal
phase transition and photosalient effect of a gold(i) isocyanide complex with shortening of
intermolecular aurophilic bonds. Chem Sci 6:1491–1497
14. (a) Shan X-C, Jiang F-L, Chen L, Wu M-Y, Pan J, Wan X-Y, Hong M-C (2013) Using
cuprophilicity as a multi-responsive chromophore switching color in response to temperature,
mechanical force and solvent vapors. J Mater Chem C 1:4339–4349. (b) Ohba T, Kobayashi A,
Chang HC, Kato M (2013) Vapour and mechanically induced chromic behaviour of platinum complexes with a dimer-of-dimer motif and the effects of heterometal ions. Dalton
Trans 42:5514–5523. (c) Choi SJ, Kuwabara J, Nishimura Y, Arai T, Kanbara T (2012) Twostep changes in luminescence color of Pt(II) complex bearing an amide moiety by mechanoand vapochromism. Chem Lett 41:65–67. (d) Zhang X, Wang JY, Ni J, Zhang LY, Chen ZN
(2012) Vapochromic and mechanochromic phosphorescence materials based on a platinum(ii)
complex with 4-trifluoromethylphenylacetylide. Inorg Chem 51:5569–5579
15. Grein F (2002) Twist angles and rotational energy barriers of biphenyl and substituted biphenyls.
J Phys Chem A 106:3823–3827
16. MacNeil DD, Decken A (1999) 2,2 -dibromobiphenyl. Acta Cryst Sect C 55:628–630
2 Biphenyl Moiety for a Solvent Responsive Aryl Gold(I) …
10. (a) Sagara Y, Mutai T, Yoshikawa I, Araki K (2007) Material design for piezochromic luminescence: hydrogen-bond-directed assemblies of a pyrene derivative. J Am Chem Soc 129:1520–
1521. (b) Ooyama Y, Kagawa Y, Fukuoka H, Ito G, Harima Y (2009) Mechanofluorochromism
of a series of benzofuro[2,3-c]oxazolo[4,5-a]carbazole-type fluorescent dyes. Eur J Org Chem
2009:5321–5326. (c) Yoon S-J, Chung JW, Gierschner J, Kim KS, Choi M-G, Kim D, Park
SY (2010) Multistimuli two-color luminescence switching via different slip-stacking of highly
fluorescent molecular sheets. J Am Chem Soc 132:13675–13683. (d) Zhang G, Lu J, Sabat
M, Fraser CL (2010) Polymorphism and reversible mechanochromic luminescence for solidstate difluoroboron avobenzone. J Am Chem Soc 132:2160–2162. (e) Sagara Y, Kato T (2011)
Brightly tricolored mechanochromic luminescence from a single-luminophore liquid crystal:
reversible writing and erasing of images. Angew Chem Int Ed 50:9128–9132. (f) Mizoshita N,
Tani T, Inagaki S (2012) Isothermally reversible fluorescence switching of a mechanochromic
perylene bisimide dye. Adv Mater 24:3350–3355. (g) Nagura K, Saito S, Yusa H, Yamawaki H,
Fujihisa H, Sato H, Shimoikeda Y, Yamaguchi S (2013) Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chromism of tetrathiazolylthiophene. J Am Chem
Soc 135:10322–10325. (h) Yagai S, Okamura S, Nakano Y, Yamauchi M, Kishikawa K, Karatsu
T, Kitamura A, Ueno A, Kuzuhara D, Yamada H, Seki T, Ito H (2014) Design amphiphilic
dipolar π-systems for stimuli-responsive luminescent materials using metastable states. Nat
Commun 5:4013. (i) Sagara Y, Lavrenova A, Crochet A, Simon Y C, Fromm K M, Weder
C (2016) A Thermo- and mechanoresponsive cyano-substituted oligo(p-phenylene vinylene)
derivative with five emissive states. Chem Eur J 22:4374–4378
11. Seki T, Ozaki T, Okura T, Asakura K, Sakon A, Uekusa H, Ito H (2015) Interconvertible
Multiple Photoluminescence Color of a Gold(I) Isocyanide Complex in the Solid State: SolventInduced Blue-Shifted and Mechano-Responsive Red-Shifted Photoluminescence. Chem Sci 6:
2187–2195
12. (a) Seki T, Sakurada K, Ito H (2013) Controlling mechano- and seeding-triggered singlecrystalto-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds.
Angew Chem Int Ed 52:12828–12832. (b) Ito H, Muromoto M, Kurenuma S, Ishizaka S,
Kitamura N, Sato H, Seki T (2013) Mechanical stimulation and solid seeding trigger singlecrystal-to-single-crystal molecular domino transformations. Nat Commun 4:2009. (c) Seki
T, Sakurada K, Ito H (2015) Mismatched changes of the photoluminescence and crystalline
structure of a mechanochromic gold(i) isocyanide complex. Chem Commun 51:13933–13936.
(d) Yagai S, Seki T, Aonuma H, Kawaguchi K, Karatsu T, Okura T, Sakon A, Uekusa H, Ito H
(2016) Mechanochromic luminescence based on crystal-to-crystal transformation mediated by
a transient amorphous state. Chem Mater 28:234–241. (e) Seki T, Takamatsu Y, Ito H (2016) A
screening approach for the discovery of mechanochromic gold(i) isocyanide complexes with
crystal-to-crystal phase transitions. J Am Chem Soc 138:6252–6260
13. Seki T, Sakurada K, Muromoto M, Ito H (2015) Photoinduced single-crystal-to-single-crystal
phase transition and photosalient effect of a gold(i) isocyanide complex with shortening of
intermolecular aurophilic bonds. Chem Sci 6:1491–1497
14. (a) Shan X-C, Jiang F-L, Chen L, Wu M-Y, Pan J, Wan X-Y, Hong M-C (2013) Using
cuprophilicity as a multi-responsive chromophore switching color in response to temperature,
mechanical force and solvent vapors. J Mater Chem C 1:4339–4349. (b) Ohba T, Kobayashi A,
Chang HC, Kato M (2013) Vapour and mechanically induced chromic behaviour of platinum complexes with a dimer-of-dimer motif and the effects of heterometal ions. Dalton
Trans 42:5514–5523. (c) Choi SJ, Kuwabara J, Nishimura Y, Arai T, Kanbara T (2012) Twostep changes in luminescence color of Pt(II) complex bearing an amide moiety by mechanoand vapochromism. Chem Lett 41:65–67. (d) Zhang X, Wang JY, Ni J, Zhang LY, Chen ZN
(2012) Vapochromic and mechanochromic phosphorescence materials based on a platinum(ii)
complex with 4-trifluoromethylphenylacetylide. Inorg Chem 51:5569–5579
15. Grein F (2002) Twist angles and rotational energy barriers of biphenyl and substituted biphenyls.
J Phys Chem A 106:3823–3827
16. MacNeil DD, Decken A (1999) 2,2 -dibromobiphenyl. Acta Cryst Sect C 55:628–630