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Tsuge K, Sawamura M (2008) Reversible mechanochromic luminescence of [(C 6 F 5 Au) 2 (μ1,4-Diisocyanobenzene)]. J Am Chem Soc 130:10044–10045. (b) Osawa M, Kawata I, Igawa
S, Hoshino M, Fukunaga T, Hashizume D (2010) Vapochromic and mechanochromic tetrahedral gold(I) complexes based on the 1,2-Bis(diphenylphosphino)benzene ligand. Chem Eur J
16:12114–12126. (c) Varughese S (2014) Non-covalent routes to tune the optical properties of
molecular materials. J Mater Chem C 2:3499–3516. (d) Gierschner J, Park S Y (2013) Luminescent distyrylbenzenes: tailoring molecular structure and crystalline morphology. J Mater
Chem C 1:5818–5832. (e) 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. (f) Zhang G, Lu J, Sabat M, Fraser CL (2010) Polymorphism
and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone. J Am
Chem Soc 132:2160–2162
3. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–143. (b) Brock CP, Schweizer WB, Dunitz JD (1991) On the validity of Wallach’s rule:
on the density and stability of racemic crystals compared with their chiral counterparts. J Am
Chem Soc 113:9811–9820
4. (a) Stine KJ, Uang JYJ, Dingman SD (1993) Comparison of enantiomeric and racemic monolayers of N-stearoyl serine methyl ester by fluorescence microscopy. Langmuir 9:2112–2118.
(b) Brammer L (2004) Developments in inorganic crystal engineering. Chem Soc Rev 33:476–
489. (c) Zhang J, Yao YG, Bu X (2007) Comparative study of homochiral and racemic chiral
metal-organic frameworks built from camphoric acid. Chem Mater 19:5083–5089. (d) Bailey AJ, Lee C, Feller RK, Orton JB, Mellot-Draznieks C, Slater B, Harrison WTA, Simoncic P, Navrotsky A, Grossel MC, Cheetham AK (2008) Comparison of chiral and racemic
forms of zinc cyclohexane trans-1,2-Dicarboxylate frameworks: a structural, computational,
and calorimetric study. Angew Chem Int Ed 47:8634–8637
5. (a) Delfs CD, Kitto HJ, Stranger R, Swiegers GF, Wild SB, Willis AC, Wilson GJ (2003)
Inorg Chem 42:4469–4478. (b) Yang EC, Zhao HK, Ding B, Wang XG, Zhao XJ (2007) Four
novel three-dimensional triazole-based zinc(II) metal–organic frameworks controlled by the
spacers of dicarboxylate ligands: hydrothermal synthesis, crystal structure, and luminescence
properties. Crys Growth Des 2009–2015. (c) McGee KA, Mann KR (2009) Inefficient crystal
packing in chiral [Ru(phen) 3 ](PF 6 ) 2 enables oxygen molecule quenching of the solid-state
MLCT emission. J Am Chem Soc 131:1896–1902. (d) Mastropietro TF, Yadav YJ, Szerb EI,
Talarico AM, Ghedini M, Crispini A (2012) Dalton Trans 41:8899–8907
6. Zhang XP, Mei JF, Lai JC, Li CH, You XZ (2015) Mechano-induced luminescent and chiroptical
switching in chiral cyclometalated platinum(II) complexes. J Mater Chem C 3:2350–2357
7. (a) 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. (b) 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: solvent-induced blue-shifted and mechano-responsive
red-shifted photoluminescence. Chem Sci 6:2187–2195. (c) Ito H, Muromoto M, Kurenuma S,
Ishizaka S, Kitamura N, Sato H, Seki T (2013) Mechanical stimulation and solid seeding trigger
single-crystal-to-single-crystal molecular domino transformations. Nat Commun 4:2009. (d)
Seki T, Sakurada K, Ito H (2013) Controlling mechano-and seeding-triggered single-crystalto-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds.
Angew Chem Int Ed 52:12828–12832
8. Bartolome C, Garcia-Cuadrado D, Ramiro Z, Espinet P (2010) Synthesis and catalytic activity
of gold chiral nitrogen acyclic carbenes and gold hydrogen bonded heterocyclic carbenes in
cyclopropanation of vinyl arenes and in intramolecular hydroalkoxylation of allenes. Inorg
Chem 49:9758–9764
101
2. (a) Ito H, Saito T, Oshima N, Kitamura N, Ishizaka S, Hinatsu Y, Wakeshima M, Kato M,
Tsuge K, Sawamura M (2008) Reversible mechanochromic luminescence of [(C 6 F 5 Au) 2 (μ1,4-Diisocyanobenzene)]. J Am Chem Soc 130:10044–10045. (b) Osawa M, Kawata I, Igawa
S, Hoshino M, Fukunaga T, Hashizume D (2010) Vapochromic and mechanochromic tetrahedral gold(I) complexes based on the 1,2-Bis(diphenylphosphino)benzene ligand. Chem Eur J
16:12114–12126. (c) Varughese S (2014) Non-covalent routes to tune the optical properties of
molecular materials. J Mater Chem C 2:3499–3516. (d) Gierschner J, Park S Y (2013) Luminescent distyrylbenzenes: tailoring molecular structure and crystalline morphology. J Mater
Chem C 1:5818–5832. (e) 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. (f) Zhang G, Lu J, Sabat M, Fraser CL (2010) Polymorphism
and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone. J Am
Chem Soc 132:2160–2162
3. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–143. (b) Brock CP, Schweizer WB, Dunitz JD (1991) On the validity of Wallach’s rule:
on the density and stability of racemic crystals compared with their chiral counterparts. J Am
Chem Soc 113:9811–9820
4. (a) Stine KJ, Uang JYJ, Dingman SD (1993) Comparison of enantiomeric and racemic monolayers of N-stearoyl serine methyl ester by fluorescence microscopy. Langmuir 9:2112–2118.
(b) Brammer L (2004) Developments in inorganic crystal engineering. Chem Soc Rev 33:476–
489. (c) Zhang J, Yao YG, Bu X (2007) Comparative study of homochiral and racemic chiral
metal-organic frameworks built from camphoric acid. Chem Mater 19:5083–5089. (d) Bailey AJ, Lee C, Feller RK, Orton JB, Mellot-Draznieks C, Slater B, Harrison WTA, Simoncic P, Navrotsky A, Grossel MC, Cheetham AK (2008) Comparison of chiral and racemic
forms of zinc cyclohexane trans-1,2-Dicarboxylate frameworks: a structural, computational,
and calorimetric study. Angew Chem Int Ed 47:8634–8637
5. (a) Delfs CD, Kitto HJ, Stranger R, Swiegers GF, Wild SB, Willis AC, Wilson GJ (2003)
Inorg Chem 42:4469–4478. (b) Yang EC, Zhao HK, Ding B, Wang XG, Zhao XJ (2007) Four
novel three-dimensional triazole-based zinc(II) metal–organic frameworks controlled by the
spacers of dicarboxylate ligands: hydrothermal synthesis, crystal structure, and luminescence
properties. Crys Growth Des 2009–2015. (c) McGee KA, Mann KR (2009) Inefficient crystal
packing in chiral [Ru(phen) 3 ](PF 6 ) 2 enables oxygen molecule quenching of the solid-state
MLCT emission. J Am Chem Soc 131:1896–1902. (d) Mastropietro TF, Yadav YJ, Szerb EI,
Talarico AM, Ghedini M, Crispini A (2012) Dalton Trans 41:8899–8907
6. Zhang XP, Mei JF, Lai JC, Li CH, You XZ (2015) Mechano-induced luminescent and chiroptical
switching in chiral cyclometalated platinum(II) complexes. J Mater Chem C 3:2350–2357
7. (a) 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. (b) 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: solvent-induced blue-shifted and mechano-responsive
red-shifted photoluminescence. Chem Sci 6:2187–2195. (c) Ito H, Muromoto M, Kurenuma S,
Ishizaka S, Kitamura N, Sato H, Seki T (2013) Mechanical stimulation and solid seeding trigger
single-crystal-to-single-crystal molecular domino transformations. Nat Commun 4:2009. (d)
Seki T, Sakurada K, Ito H (2013) Controlling mechano-and seeding-triggered single-crystalto-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds.
Angew Chem Int Ed 52:12828–12832
8. Bartolome C, Garcia-Cuadrado D, Ramiro Z, Espinet P (2010) Synthesis and catalytic activity
of gold chiral nitrogen acyclic carbenes and gold hydrogen bonded heterocyclic carbenes in
cyclopropanation of vinyl arenes and in intramolecular hydroalkoxylation of allenes. Inorg
Chem 49:9758–9764