Fréchet-type dendrons bearing azobenzene units and flexible oligo(ethylene glycol) spacers: synthesis, characterization, thermal and optical properties

References

• Fréchet , JMJ and Tomalia , D . 2002 . Dendrimers and other dendritric polymers , New York , NY : Wiley .
   Google Scholar
• Newkome , GR , Vögtle , F and Moorefield , CN . 2001 . Dendrimers and dendrons , Weinheim : Wiley-VCH .
   Google Scholar
• Newkome , GR and Shreiner , CD . 2008 . Poly(amidoamine), polypropylenimine, and related dendrimers and dendrons possessing different 1/2 branching motifs: an overview of the divergent procedures . Polymer , 49 : 1 – 173 .
   Web of Science ®Google Scholar
• Jean-Pierre , Majoral and Anne-Marie , Caminade . 1999 . Dendrimers containing heteroatoms (Si, P, B, Ge, or Bi) . Chem. Rev. , 99 : 845 – 880 .
   PubMed Web of Science ®Google Scholar
• Vögtle , F , Richardt , G and Werner , N . 2009 . Dendrimer chemistry , Weinheim : Wiley-VCH .
   Google Scholar
• Momotake , A and Arai , T . 2004 . Synthesis, excited state properties, and dynamic structural change of photoresponsive dendrimers . Polymer. , 45 : 5369 – 5390 .
   Web of Science ®Google Scholar
• Momotake , A and Arai , T . 2004 . Photochemistry and photophysics of stilbene dendrimers and related compounds . J. Photochem. Photobiol. C. Photochem. Rev. , 5 : 1 – 25 .
   Web of Science ®Google Scholar
• Shibaev , V , Bobrovsky , A and Boiko , N . 2003 . Photoactive liquid crystalline polymer systems with light-controllable structure and optical properties . Prog. Polym. Sci. , 28 : 729 – 836 .
   Web of Science ®Google Scholar
• Villavicencio , O and McGrath , DV . 2002 . Advances in dendritic . Macromolecules , 5 : 1 – 44 .
   Google Scholar
• Deloncle R, Caminade Anne-Marie. Stimuli-responsive dendritic structures: the case of light-driven azobenzene-containing dendrimers and dendrons. J. Photochem. Photobiol. C. Photochem. Rev. 2010;11:25–45.
   Google Scholar
• Mekelburger , HB , Rissanen , K and Vögtle , F . 1993 . Repetitive-synthesis of bulky dendrimers a reversibly photoactive dendrimers with six azobenzene side chains . Chem. Ber. , 126 : 1161 – 1169 .
   Google Scholar
• Buhleier , EW , Wehner , W and Vögtle , F . 1978 . Cascade and nonskid-chain-like syntheses of molecular cavity topologies . Synthesis , 2 : 155 – 158 .
   Google Scholar
• Wörner , C and Mülhaupt , R . 1993 . Polynitrile and polyamine funtional poly(trimethylene imine) dendrimers . Angew. Chem. Int. Ed. Engl. , 32 : 1306 – 1308 .
   Web of Science ®Google Scholar
• De Brabander-van den Berg EMM, Meijer EW. Poly(propylene imine) dendrimers: large-scale synthesis by hetereogeneously catalyzed hydrogenations. Angew. Chem. Int. Ed. Engl. 1993;32:1308–1311.
   Google Scholar
• Archut , A , Vögtle , F , De Cola , L , Azzellini , GC , Balzani , V , Ramanujam , PS and Berg , RH . 1998 . Azobenzene-functionalized cascade molecules: photoswitchable supramolecular systems . Chem. Eur. J. , 4 : 699 – 706 .
   Web of Science ®Google Scholar
• Dirksen , A , Zuidema , E , Williams , RM , De Cola , L , Kauffmann , C , Vögtle , F , Roque , A and Pina , F . 2002 . Photoactivity and pH sensitivity of methyl orange functionalized poly(propyleneamine) dendrimers . Macromolecules , 35 : 2743 – 2747 .
   Web of Science ®Google Scholar
• Schenning , AP , Elissen-Roman , C , Weener , JW , Baars , MW , Van der Gaast , SJ and Meijer , EW . 1998 . Amphiphilic dendrimers as building blocks in supramolecular assemblies . J. Am. Chem. Soc. , 120 : 8199 – 8208 .
   Web of Science ®Google Scholar
• Alcala , R , Gimenez , R , Oriol , L , Pinol , M , Serrano , JL , Villacampa , B and Vinuales , AI . 2007 . Synthesis, characterization, and induction of stable anisotropy in liquid crystalline photo-addressable PPI dendrimers . Chem. Mater. , 19 : 235 – 246 .
   Web of Science ®Google Scholar
• Tomalia , DA , Baker , H , Dewald , J , Hall , M , Kallos , G , Martin , S , Roeck , J , Ryder , J and Smith , P . 1985 . A new class of polymers: starburts-dendritic macromolecules . Polym. J. , 17 : 117 – 132 .
   Web of Science ®Google Scholar
• Hawker , CJ and Fréchet , JMJ . 1990 . Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules . J. Am. Chem. Soc. , 112 : 7638 – 7647 .
   Web of Science ®Google Scholar
• Li S, McGrath DV. Macromolecular isomers of azobenzene-containing photochromic dendrimers. Polym. Prep. (Am. Chem. Soc., Div. Polym. Chem.) 2000;41:861–864.
   Google Scholar
• Li , S and McGrath , DV . 2000 . Effect of macromolecular isomerism on the photomodulation of dendrimer properties . J. Am. Chem. Soc. , 122 : 6795 – 6796 .
   Web of Science ®Google Scholar
• Nithyanandhan , J , Jayaraman , N , Davis , R and Das , S . 2004 . Synthesis, fluorescence and photoisomerization studies of azobenzene-functionalized poly(alkyl aryl ether) dendrimers . Chem. Eur. J. , 10 : 689 – 698 .
   PubMed Web of Science ®Google Scholar
• Kay , KY , Han , KJ , Yu , YJ and Park , YD . 2002 . Dendritic fullerenes (C60) with photoresponsive azobenzene groups . Tetrahedron Lett. , 43 : 5053 – 5056 .
   Web of Science ®Google Scholar
• Rau H. Photisomerization of azobenzenes. In: Rabek JK, editor. Photochemistry and photophysics. Vol. 2. Boca Raton (FL): CRC Press; 1990. Chapter 4; p. 119–141.
   Google Scholar
• Natansohn , A and Rochon , P . 2001 . 2000 macromolecular science and engineering award lecture the versatility of azobenzene polymers . Can. J. Chem. , 79 : 1093 – 1100 .
   Web of Science ®Google Scholar
• Todorov , T , Nikalova , L and Tomova , N . 1984 . Polarization holography. 1: a new high-efficiency organic material with reversible photoinduced birefringence . Appl. Opt. , 23 : 4309 – 4312 .
   PubMed Web of Science ®Google Scholar
• Xie , S , Natansohn , A and Rochon , P . 1993 . Recent developments in aromatic azo polymers research . Chem. Mater. , 5 : 403 – 411 .
   Web of Science ®Google Scholar
• Viswanathan , NK , Kim , DY , Bian , S , Williams , J , Liu , W , Li , L , Samuelson , L , Kumar , J and Tripathy , SK . 1999 . Surface relief structures on azo polymer films . J. Mater. Chem. , 9 : 1941 – 1955 .
   Web of Science ®Google Scholar
• Ichimura , K . 2000 . Photoalignment of liquid-crystal systems . Chem. Rev. , 100 : 1847 – 1874 .
   PubMed Web of Science ®Google Scholar
• Delaire , JA and Nakatani , K . 2000 . Linear and nonlinear optical properties of photochromic molecules and materials . Chem. Rev. , 100 : 1817 – 1846 .
   PubMed Web of Science ®Google Scholar
• Natansohn , A and Rochon , P . 2002 . Photoinduced motions in azo containing polymers . Chem. Rev. , 102 : 4139 – 4175 .
   PubMed Web of Science ®Google Scholar
• Kasha , M . 1963 . Energy transfer mechanisms and the molecular exciton model for molecular aggregates . Radiat. Res. , 20 : 55 – 71 .
   PubMed Web of Science ®Google Scholar
• Dircio , J , Gelover-Santiago , A , Caicedo , C , Carreón-Castro , MP , Valdez-Hernández , Y and Rivera , E . 2012 . Synthesis and characterization of novel polythiophenes containing azobenzene units and well-defined oligo(ethylene glycol) spacers: thermal and optical properties, and preparation of langmuir films . Des. Monomers Polym. , 15 : 175 – 195 .
   Web of Science ®Google Scholar
• Buruiana , EC , Zamfir , M , Melinte , V and Buruiana , T . 2010 . Photo-polymers containing (S)-phenylalanine and stilbene pendants: synthesis and properties of ionic polyacrylates . Des. Monomers Polym. , 13 : 21 – 32 .
   Web of Science ®Google Scholar
• Nicolescu , FA , Jerca , VV , Draghici , C , Vuluga , DM and Vasilescu , DS . 2009 . Synthesis and characterization of novel azobenzene methacrylate monomers . Des. Monomers Polym. , 12 : 553 – 563 .
   Web of Science ®Google Scholar
• Kıskan , B , Dogan , F , Durmaz , YY and Yagc , Y . 2008 . Synthesis, characterization and thermally-activated curing of azobenzene-containing benzoxazines . Des. Monomers Polym. , 11 : 473 – 482 .
   Web of Science ®Google Scholar
• Buruiana , EC , Buruiana , T , Zamfir , M , Pohoata , V and Donescu , D . 2008 . Elastomeric azo-polyurethanes containing fluorescent pyrene and their photo activity . Des. Monomers Polym. , 10 : 347 – 360 .
   Web of Science ®Google Scholar
• Huang , D , Zhang , C , Dalton , LR and Weber , WP . 2000 . Sequential synthesis of main-chain NLO oligomers which contain 4-dialkylamino-4′-(alkylsulfonyl)azobenzene chromophores . Des. Monomers Polym. , 3 : 95 – 111 .
   Web of Science ®Google Scholar
• He , X , Zhang , HL , Yan , DL and Wang , X . 2003 . Synthesis of side-chain liquid-crystalline homopolymers and triblock copolymers with p-methoxyazobenzene moieties and poly(ethylene glycol) as coil segments by atom transfer radical polymerization and their thermotropic phase behavior . J. Polym. Sci., Part A: Polym. Chem. , 41 : 2854 – 2864 .
   Web of Science ®Google Scholar
• Tian , YQ , Watanabe , K , Kong , XX , Abe , J and Iyoda , T . 2002 . Synthesis, nanostructures, and functionality of amphiphilic liquid crystalline block copolymers with azobenzene moieties . Macromolecules , 35 : 3739 – 3747 .
   Web of Science ®Google Scholar
• Saito , M , Shimomura , T , Okumura , Y , Ito , K and Hayakawa , R . 2001 . Temperature dependence of inclusion-dissociation behavior between molecular nanotubes and linear polymers . J. Chem. Phys. , 114 : 1 – 3 .
   Web of Science ®Google Scholar
• Shimomura , T , Funaki , T and Ito , K . 2002 . Circular dichroism study of the inclusion-dissociation behavior of complexes between a molecular nanotube and azobenzene substituted linear polymers . J. Incl. Phenom. Macroc. Chem. , 44 : 275 – 278 .
   Web of Science ®Google Scholar
• Zheng , PJ , Wang , C , Hu , X , Tam , KC and Li , L . 2005 . Supramolecular complexes of azocellulose and R-cyclodextrin: isothermal titration calorimetric and spectroscopic studies . Macromolecules , 38 : 2859 – 2864 .
   Web of Science ®Google Scholar
• Hu , X , Zheng , PJ , Zhao , XY , Li , L , Tam , KC and Gan , LH . 2004 . Preparation, characterization and novel photoregulated rheological properties of azobenzene functionalized cellulose derivatives and their α-CD complexes . Polymer , 45 : 6219 – 6225 .
   Web of Science ®Google Scholar
• Takashima , Y , Nakayama , T , Miyauchi , M and Kawaguchi , Y . 2004 . Complex formation and gelation between copolymers containing pendant azobenzene groups and cyclodextrin polymers . Chem. Lett. , 33 : 890 – 891 .
   Web of Science ®Google Scholar
• Ikeda , T , Ooya , T and Yui , N . 1999 . Regulation of pseudo-polyrotaxane formation between α–cyclodetrins and azobenzene-terminated poly(ethylene glycol) . Polym. J. , 31 : 658 – 663 .
   Web of Science ®Google Scholar
• Tung , CH , Wu , LZ , Zhang , LP and Chen , B . 2003 . Supramolecular systems as microreactors: control of product selectivity in organic phototransformation . Acc. Chem. Res. , 36 : 39 – 47 .
   PubMed Web of Science ®Google Scholar
• Rivera , E , Belletête , M , Natansohn , A and Durocher , G . 2003 . Synthesis characterization and optical properties of a novel azo-dye bearing an oligo(ethylene glycol) methyl ether side chain in solution and in the solid state . Can. J. Chem. , 81 : 1076 – 1082 .
   Web of Science ®Google Scholar
• Rivera , E , Carreón-Castro , MP , Buendía , I and Cedillo , G . 2006 . Optical properties and aggregation of novel azo-dyes bearing an end-capped oligo(ethylene glycol) side chain in solution, solid state and langmuir-blodgett films . Dyes Pigm. , 68 : 217 – 226 .
   Web of Science ®Google Scholar
• Rivera , E , Carreón-Castro , MP , Salazar , R , Huerta , G , Becerril , C and Rivera , L . 2007 . Preparation and characterization of novel grafted polyethylene based azo-polymers bearing oligo(ethylene glycol) spacers . Polymer. , 48 : 3420 – 3428 .
   Web of Science ®Google Scholar
• García , T , Carreón-Castro , MP , Gelover-Santiago , A , Ponce , P , Romero , M and Rivera , E . 2012 . Synthesis and characterization of novel amphiphilic azo-polymers bearing well-defined oligo(ethylene glycol) spacers . Des. Monomers Polym. , 15 : 159 – 174 .
   Web of Science ®Google Scholar
• Caicedo , C , Rivera , E , Valdez-Hernández , Y and Carreón-Castro , MP . 2011 . Synthesis and characterization of novel liquid-crystalline azo-dyes bearing two amino-nitro substituted azobenzene units and a well-defined, oligo(ethylene glycol) spacer . Mater. Chem. Phys. , 130 : 471 – 480 .
   Web of Science ®Google Scholar
• Alvarez-Venicio , V , Jiménez-Nava , B , Carreón-Castro , MP , Rivera , E , Méndez , IA , Huerta , AA and Gutiérrez-Nava , M . 2008 . Synthesis and incorporation in Langmuir films of oligophenylenevinylene dendrimers bearing a polar head group and different dendritic poly(benzyl ether) branches . Polymer. , 49 : 3911 – 3922 .
   Web of Science ®Google Scholar
• Lagugne-Labarthet , F , Freiberg , S , Pellerin , C , Pezolet , M , Natansohn , A and Rochon , P . 2000 . Spectroscopic and optical characterization of a series of azobenzene-containing side-chain liquid crystalline polymers . Macromolecules. , 33 : 6815 – 6823 .
   Web of Science ®Google Scholar