126
4 Mechano-Responsive Luminescence via Crystal-to-Crystal Phase …
J Am Chem Soc 132:2160–2162. (e) 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 (μ-1,4-Diisocyanobenzene)]. J Am Chem Soc 130:10044–10045. (f)
Jin M, Seki T, Ito H (2016) Luminescent mechanochromism of a chiral complex: distinct crystal structures and color changes of racemic and homochiral gold(I) isocyanide complexes with
a binaphthyl moiety. Chem Commun 52:8083–8086
3. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–143. (b) Brock CP, Schweizer W B, Dunitz J D (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. Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press
5. Mercier N, Barres A-L, Giffard M, Rau I, Kajzar F, Sahraoui B (2006) Conglomerate-to-trueracemate reversible solid-state transition in crystals of an organic disulfide-based iodoplumbate.
Angew Chem Int Ed 45:2100–2103
6. (a) 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. (b) Harada N, Abe Y, Karasawa S, Koga N (2012)
Polymorphic equilibrium responsive thermal and mechanical stimuli in light-emitting crystals of N-Methylaminonaphthyridine. Org Lett 14: 6282-6285. (c) Abe Y, Karasawa S, Koga
N (2012) Crystal structures and emitting properties of trifluoromethylaminoquinoline derivatives: thermal single-crystal-to-single-crystal transformation of polymorphic crystals that emit
different colors. Chem Eur J 18:15038–15048. (d) 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. (e) 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. (f) 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 mechanoresponsive red-shifted photoluminescence. Chem Sci 6:2187–2195. (g) 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
7. (a) 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. (b) Seki T, Sakurada K, Ito H (2013) Controlling mechano-and seeding-triggered single-crystal-to-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds. Angew Chem Int Ed 52:12828–12832.
(c) Seki T, Sakurada K, Muromoto M, Seki S, Ito H (2016) Detailed investigation of the structural, thermal, and electronic properties of gold isocyanide complexes with mechano-triggered
single-crystal-to-single-crystal phase transitions. Chem Eur J 22:1968–1978
8. Krasovskiy A, Malakhov V, Gavryushin A, Knochel P (2006) efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides.
Angew Chem Int Ed 45:6040–6044
9. Hong Y, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40:5361–
5388
10. Sheldrick GM (2013) Program for the refinement of crystal structures. University of Göttingen,
Göttingen (SHELXL-2013)
11. Frisch MJ et al (2009) Gaussian 09 revision C.01, Gaussian Inc. Wallingford
12. Spartan ’10. Wavefunction, Inc. Irvine
4 Mechano-Responsive Luminescence via Crystal-to-Crystal Phase …
J Am Chem Soc 132:2160–2162. (e) 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 (μ-1,4-Diisocyanobenzene)]. J Am Chem Soc 130:10044–10045. (f)
Jin M, Seki T, Ito H (2016) Luminescent mechanochromism of a chiral complex: distinct crystal structures and color changes of racemic and homochiral gold(I) isocyanide complexes with
a binaphthyl moiety. Chem Commun 52:8083–8086
3. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–143. (b) Brock CP, Schweizer W B, Dunitz J D (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. Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press
5. Mercier N, Barres A-L, Giffard M, Rau I, Kajzar F, Sahraoui B (2006) Conglomerate-to-trueracemate reversible solid-state transition in crystals of an organic disulfide-based iodoplumbate.
Angew Chem Int Ed 45:2100–2103
6. (a) 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. (b) Harada N, Abe Y, Karasawa S, Koga N (2012)
Polymorphic equilibrium responsive thermal and mechanical stimuli in light-emitting crystals of N-Methylaminonaphthyridine. Org Lett 14: 6282-6285. (c) Abe Y, Karasawa S, Koga
N (2012) Crystal structures and emitting properties of trifluoromethylaminoquinoline derivatives: thermal single-crystal-to-single-crystal transformation of polymorphic crystals that emit
different colors. Chem Eur J 18:15038–15048. (d) 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. (e) 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. (f) 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 mechanoresponsive red-shifted photoluminescence. Chem Sci 6:2187–2195. (g) 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
7. (a) 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. (b) Seki T, Sakurada K, Ito H (2013) Controlling mechano-and seeding-triggered single-crystal-to-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds. Angew Chem Int Ed 52:12828–12832.
(c) Seki T, Sakurada K, Muromoto M, Seki S, Ito H (2016) Detailed investigation of the structural, thermal, and electronic properties of gold isocyanide complexes with mechano-triggered
single-crystal-to-single-crystal phase transitions. Chem Eur J 22:1968–1978
8. Krasovskiy A, Malakhov V, Gavryushin A, Knochel P (2006) efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides.
Angew Chem Int Ed 45:6040–6044
9. Hong Y, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40:5361–
5388
10. Sheldrick GM (2013) Program for the refinement of crystal structures. University of Göttingen,
Göttingen (SHELXL-2013)
11. Frisch MJ et al (2009) Gaussian 09 revision C.01, Gaussian Inc. Wallingford
12. Spartan ’10. Wavefunction, Inc. Irvine