146
4 Applications of Nitrile Imine Derivatives
63. Yu Z, Ho LY, Lin Q (2011) Rapid, photoactivatable turn-on fluorescent probes based on an
intramolecular photoclick reaction. J Am Chem Soc 133:11912–11915
64. Zengeya TT, Garlick JM, Kulkarni RA, Miley M, Roberts AM, Yang Y, Crooks DR, Sourbier
C, Linehan WM, Meier JL (2016) Co-opting a bioorthogonal reaction for oncometabolite
detection. J Am Chem Soc 138:15813–15816
65. Kulkarni RA, Briney CA, Crooks DR, Bergholtz SE, Mushti C, Lockett SJ, Lane AN, Fan
TW-M, Swenson RE, Marston Linehan W, Meier JL (2019) Photoinducible oncometabolite
detection. ChemBioChem 20:360–365
66. An P, Lewandowski TM, Lin Q (2018) Design and synthesis of a BODIPY-tetrazole based
“Off-On” in-cell fluorescence reporter of hydrogen peroxide. ChemBioChem 19:1326–1333
67. Schart VF, Hassenrück J, Späte A-K, Dold JEGA, Fahrner R, Wittmann V (2019) Triple
orthogonal labeling of glycans by applying photoclick chemistry. ChemBioChem 20:166–171
68. Song W, Yu Z, Madden MM, Lin Q (2010) A bioorthogonal chemistry strategy for probing
protein lipidation in live cells. Mol BioSyst 6:1576
69. Stille JK, Harris FW (1966) Polymers from 1,3-dipole addition reactions: the Nitrilimine
dipole. J Polym Sci Part B Polym Lett 4:333–336
70. Iwakura Y, Shiraishi S, Akiyama M (1966) Polymerizations by 1,3-dipolar cycloaddition
reactions. IV. N, N -Diphenylterephthalonitrilimine. Die Makromol Chemie 97:278–281
71. Stille JK, Gotter LD (1968) Polymers from 1,3-dipole addition reactions: a Bis nitrilimine
dipole from a Bis tetrazole precursor. J Polym Sci Part B Polym Lett 6:11–14
72. Stille JK, Harris FW (1968) Polymers from 1,3-dipole addition reactions: the Nitrilimine
dipole from acid hydrazide chlorides. J Polym Sci Part A-1 Polym Chem 6:2317–2330
73. Estupiñán D, Gegenhuber T, Blinco JP, Barner-Kowollik C, Barner L (2017) Self-reporting
fluorescent step-growth RAFT polymers based on nitrile imine-mediated tetrazole-ene
cycloaddition chemistry. ACS Macro Lett 6:229–234
74. Sayed AR, Wiggins JS (2008) 1,3-dipolar cycloaddition polymerization reactions of novel
macromolecules containing Sym-tetrazine rings. Polymer (Guildf) 49:2253–2259
75. Sayed AR, Wiggins JS (2011) Alternating copolymer of pyridine and 1,4-diphenyl-1,2,4,5Tetrazine from Bis-1,3-dipolar cycloaddition polymerization. J Appl Polym Sci 120:623–630
76. Stille JK, Gotter LD (1969) 1,3-dipolar addition polymerizations. The synthesis and 1,3dipolar addition polymerization of dipole-dipolarophile (A-B) monomers containing Tetrazole
and vinyl or ethynyl moieties. Macromolecules 2:465–468
77. Mueller JO, Voll D, Schmidt FG, Delaittre G, Barner-Kowollik C (2014) Fluorescent polymers
from non-fluorescent photoreactive monomers. Chem Commun 50:15681–15684
78. Dürr CJ, Lederhose P, Hlalele L, Abt D, Kaiser A, Brandau S, Barner-Kowollik C (2013)
Photo-induced ligation of acrylonitrile-butadiene rubber: selective tetrazole-ene coupling of
chain-end-functionalized copolymers of 1,3-butadiene. Macromolecules 46:5915–5923
79. Hiltebrandt K, Pauloehrl T, Blinco JP, Linkert K, Borner HG, Barner-Kowollik C (2015)
λ-orthogonal pericyclic macromolecular photoligation. Angew Chem Int Ed Engl 54:2838–43
80. Rudin A, Choi P, Rudin A, Choi P (2013) Free-radical polymerization, 3rd edn. Academic
Press, Cambridge
81. Stille JK, Gotter LD (1969) Free-radical polymerization of 2-phenyl-5-(4’vinyl)phenyltetrazole. Reactivity ratios and Q and e values. Macromolecules
2:468–474
82. Stille JK, Chen AT (1972) Synthesis and copolymerization of styryl-substituted Tetrazoles.
Thermal cross-linking of copolymers containing dipolarophiles and the Tetrazoles as Nitrile
Imine dipole precursors. Macromolecules 5:377–384
83. Darkow R, Yoshikawa M, Kitao T, Tomaschewski G, Schellenberg J (1994) Photomodification
of a Poly(acrylonitrile-co-butadiene-co-styrene) containing Diaryltetrazolyl groups. J Polym
Sci Part A Polym Chem 32:1657–1664
84. Darkow R, Hartmann U, Tomaschewski G (1997) Synthesis, photomodification and characterization of homo- and copolymers with 2,5-Bis aryltetrazolyl pendant groups. React Funct
Polym 32:195–207
4 Applications of Nitrile Imine Derivatives
63. Yu Z, Ho LY, Lin Q (2011) Rapid, photoactivatable turn-on fluorescent probes based on an
intramolecular photoclick reaction. J Am Chem Soc 133:11912–11915
64. Zengeya TT, Garlick JM, Kulkarni RA, Miley M, Roberts AM, Yang Y, Crooks DR, Sourbier
C, Linehan WM, Meier JL (2016) Co-opting a bioorthogonal reaction for oncometabolite
detection. J Am Chem Soc 138:15813–15816
65. Kulkarni RA, Briney CA, Crooks DR, Bergholtz SE, Mushti C, Lockett SJ, Lane AN, Fan
TW-M, Swenson RE, Marston Linehan W, Meier JL (2019) Photoinducible oncometabolite
detection. ChemBioChem 20:360–365
66. An P, Lewandowski TM, Lin Q (2018) Design and synthesis of a BODIPY-tetrazole based
“Off-On” in-cell fluorescence reporter of hydrogen peroxide. ChemBioChem 19:1326–1333
67. Schart VF, Hassenrück J, Späte A-K, Dold JEGA, Fahrner R, Wittmann V (2019) Triple
orthogonal labeling of glycans by applying photoclick chemistry. ChemBioChem 20:166–171
68. Song W, Yu Z, Madden MM, Lin Q (2010) A bioorthogonal chemistry strategy for probing
protein lipidation in live cells. Mol BioSyst 6:1576
69. Stille JK, Harris FW (1966) Polymers from 1,3-dipole addition reactions: the Nitrilimine
dipole. J Polym Sci Part B Polym Lett 4:333–336
70. Iwakura Y, Shiraishi S, Akiyama M (1966) Polymerizations by 1,3-dipolar cycloaddition
reactions. IV. N, N -Diphenylterephthalonitrilimine. Die Makromol Chemie 97:278–281
71. Stille JK, Gotter LD (1968) Polymers from 1,3-dipole addition reactions: a Bis nitrilimine
dipole from a Bis tetrazole precursor. J Polym Sci Part B Polym Lett 6:11–14
72. Stille JK, Harris FW (1968) Polymers from 1,3-dipole addition reactions: the Nitrilimine
dipole from acid hydrazide chlorides. J Polym Sci Part A-1 Polym Chem 6:2317–2330
73. Estupiñán D, Gegenhuber T, Blinco JP, Barner-Kowollik C, Barner L (2017) Self-reporting
fluorescent step-growth RAFT polymers based on nitrile imine-mediated tetrazole-ene
cycloaddition chemistry. ACS Macro Lett 6:229–234
74. Sayed AR, Wiggins JS (2008) 1,3-dipolar cycloaddition polymerization reactions of novel
macromolecules containing Sym-tetrazine rings. Polymer (Guildf) 49:2253–2259
75. Sayed AR, Wiggins JS (2011) Alternating copolymer of pyridine and 1,4-diphenyl-1,2,4,5Tetrazine from Bis-1,3-dipolar cycloaddition polymerization. J Appl Polym Sci 120:623–630
76. Stille JK, Gotter LD (1969) 1,3-dipolar addition polymerizations. The synthesis and 1,3dipolar addition polymerization of dipole-dipolarophile (A-B) monomers containing Tetrazole
and vinyl or ethynyl moieties. Macromolecules 2:465–468
77. Mueller JO, Voll D, Schmidt FG, Delaittre G, Barner-Kowollik C (2014) Fluorescent polymers
from non-fluorescent photoreactive monomers. Chem Commun 50:15681–15684
78. Dürr CJ, Lederhose P, Hlalele L, Abt D, Kaiser A, Brandau S, Barner-Kowollik C (2013)
Photo-induced ligation of acrylonitrile-butadiene rubber: selective tetrazole-ene coupling of
chain-end-functionalized copolymers of 1,3-butadiene. Macromolecules 46:5915–5923
79. Hiltebrandt K, Pauloehrl T, Blinco JP, Linkert K, Borner HG, Barner-Kowollik C (2015)
λ-orthogonal pericyclic macromolecular photoligation. Angew Chem Int Ed Engl 54:2838–43
80. Rudin A, Choi P, Rudin A, Choi P (2013) Free-radical polymerization, 3rd edn. Academic
Press, Cambridge
81. Stille JK, Gotter LD (1969) Free-radical polymerization of 2-phenyl-5-(4’vinyl)phenyltetrazole. Reactivity ratios and Q and e values. Macromolecules
2:468–474
82. Stille JK, Chen AT (1972) Synthesis and copolymerization of styryl-substituted Tetrazoles.
Thermal cross-linking of copolymers containing dipolarophiles and the Tetrazoles as Nitrile
Imine dipole precursors. Macromolecules 5:377–384
83. Darkow R, Yoshikawa M, Kitao T, Tomaschewski G, Schellenberg J (1994) Photomodification
of a Poly(acrylonitrile-co-butadiene-co-styrene) containing Diaryltetrazolyl groups. J Polym
Sci Part A Polym Chem 32:1657–1664
84. Darkow R, Hartmann U, Tomaschewski G (1997) Synthesis, photomodification and characterization of homo- and copolymers with 2,5-Bis aryltetrazolyl pendant groups. React Funct
Polym 32:195–207