With Tag: Photographic Sensitizers

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Efficient Synthesis and Properties of Novel Near-Infrared Electrochromic Anthraquinone Imides

Naiheng Song, Wenqiang Qiao, Zhi Yuan Wang, Jia Zheng, Yijun Zheng, Yufeng Wang, Xinhua Wan
Org. Lett. | 2008 | 10.1021/ol703001s

An efficient synthesis of novel near-infrared electrochromic 6-substituted (NO 2 , Br) anthraquinone imides, i.e., 2a and 2b, was established. Bearing functional groups suitable for further structural modifications by nucleophilic substitution reaction and...


Calix[4]arene-Functionalized Naphthalene and Perylene Imide Dyes

Volker Böhmer, Chang-Cheng You, Frank Würthner, Myroslav O. Vysotsky, Kari Rissanen
Org. Lett. | 2002 | 10.1021/ol026402o

Calix[4]arenes bearing one, two, or four 1,8-naphthyl imide groups at the wide rim and bis-calix[4]arenes connected via perylene-bisimide dye spacers have been synthesized. The low-temperature NMR spectrum of the tetranaphthylimide suggests, in agreement with...


Unprecedented Binary Cu(I)/Cu(II) Catalyzed One-Pot, Three-Component Synthesis and Evaluation of Luminescent Property of 2-Amino-3-iminoethenylidene-2-indolones: A New Class of Merocyanine Dye Analogues

Somasundharam Periyaraja, Asit Baran Mandal, Ponnusamy Shanmugam
Org. Lett. | 2011 | 10.1021/ol2022164

A facile and efficient binary Cu(I)/Cu(II) catalyzed one-pot, three-component synthesis of 2-amino-3-iminoethenylidene-2-indolones in excellent yield has been achieved. Remarkably, these newly synthesized, stable merocyanine dye analogues showed strong...


Tetrastyryl-BODIPY-Based Dendritic Light Harvester and Estimation of Energy Transfer Efficiency

Ziya Kostereli, Onur Buyukcakir, Tugba Ozdemir, Engin U. Akkaya
Org. Lett. | 2012 | 10.1021/ol301462x

Versatile BODIPY dyes can be transformed into bright near-IR-emitting fluorophores by quadruple styryl substitutions. When clickable functionalities on the styryl moieties are inserted, an efficient synthesis of a light harvester is possible. In addition,...


Synthesis and Properties of Novel C3-Symmetric Coplanar Chromophores

Jia-Hong Chen, Yi-Hung Liu, Shao-An Wang, Ken-Tsung Wong
Org. Lett. | 2011 | 10.1021/ol201466z

New synthetic pathways for novel C 3 -symmetric molecules featured with a thiophene-fused six-five-five carbon-bridged coplanar core structure have been established. The incorporation of thiophene as the constituent of a C 3 -symmetric core provides effective...


Syntheses and Structures of Novel Heteroarene-Fused Coplanar π-Conjugated Chromophores

Liang-Chen Chi, Ken-Tsung Wong, Shih-Feng Chiu, Yu Wang, Yi-Hung Liu, Ying-Ying Chu, Teng-Chih Chao, Akula Balaiah
Org. Lett. | 2006 | 10.1021/ol061791y

We have synthesized a series of novel coplanar chromophores in which heteroarenes, namely, thiophene, benzothiophene, and carbazole, were fused to neighboring phenylene ring(s) through intramolecular annulation via sp 3 -hybridized carbon atoms bearing two...


Stable Near-Infrared Anionic Polymethine Dyes: Structure, Photophysical, and Redox Properties

Loïc Toupet, Chantal Andraud, Pierre-Antoine Bouit, Olivier Maury, Stéphane Rigaut, Christophe Aronica, Emmanuel Di Piazza, Boris Le Guennic
Org. Lett. | 2008 | 10.1021/ol801416n



Synthesis of Diphenylamine-Based Novel Fluorescent Styryl Colorants by Knoevenagel Condensation Using a Conventional Method, Biocatalyst, and Deep Eutectic Solvent

Sunanda B. Phadtare, Amit R. Jagtap, Ganapati S. Shankarling, Bhushan N. Borse, Yogesh A. Sonawane
Org. Lett. | 2010 | 10.1021/ol902976u

Novel Y-shaped acceptor−π-donor−π-acceptor-type compounds, synthesized from 4,4′-hexyliminobisbenzaldehyde as electron donors and different active methylene compounds as electron acceptors, were produced by conventional Knoevenagel condensation alone, with a...


Cyclohexenylphenyldiazene:  A Simple Surrogate of the Azobenzene Photochromic Unit

Alberto Credi, Irene Conti, Filippo Marchioni, Goffredo Rosini, Giorgio Orlandi, Marco Garavelli
J. Am. Chem. Soc. | 2007 | 10.1021/ja0668466

We have carried out an experimental and computational study on the ground- and excited-state photochemical and photophysical properties of (1-cyclohexenyl)phenyldiazene (CPD), a species formally derived from azobenzene in which one of the phenyl rings is...


Direct Synthesis of Fluorescent 1,3a,6a-Triazapentalene Derivatives via Click–Cyclization–Aromatization Cascade Reaction

Shoji Ishizaka, Keiji Tanino, Ayumi Osawa, Noboru Kitamura, Kosuke Namba
J. Am. Chem. Soc. | 2011 | 10.1021/ja203917r

An efficient and versatile method was established for the preparation of 1,3a,6a-triazapentalenes. The 1,3a,6a-triazapentalene skeleton without an additional fused ring system was discovered to be a compact and highly fluorescent chromophore, which exhibited...


Distinct Responses to Mechanical Grinding and Hydrostatic Pressure in Luminescent Chromism of Tetrathiazolylthiophene

Hitoshi Yusa, Shigehiro Yamaguchi, Yuichi Shimoikeda, Shohei Saito, Kazuhiko Nagura, Hiroyasu Sato, Hiroshi Fujihisa, Hiroshi Yamawaki
J. Am. Chem. Soc. | 2013 | 10.1021/ja4055228

Luminescent mechanochromism has been intensively studied in the past few years. However, the difference in the anisotropic grinding and the isotropic compression is not clearly distinguished in many cases, in spite of the importance of this discrimination for...


Femtosecond Dynamics of a Simple Merocyanine Dye:  Does Deprotonation Compete with Isomerization?

C. Burda, M. H. Abdel-Kader, M. A. El-Sayed, S. Link
J. Am. Chem. Soc. | 2000 | 10.1021/ja993940w

The primary photochemistry of the trans isomer of a simple merocyanine dye of the stilbazolium betaine type 1-methyl-4-(4‘-hydroxytyryl)pyridinium betaine (M trans ) and its conjugate acid MH + trans in aqueous solution is studied by femtosecond...


Double Lactonization in Triarylamine-Conjugated Dimethyl Diethynylfumarate: Formation of Intensely Colored and Luminescent Quadrupolar Molecules Including a Missing Structural Isomer of Pechmann Dyes

Mikihiro Hayashi, Ryota Sakamoto, Fumiyuki Toshimitsu, Hiroshi Nishihara
J. Am. Chem. Soc. | 2011 | 10.1021/ja2054176

Acid-induced double lactonization in triarylamine-conjugated dimethyl diethynylfumarate E-1 opens up a new synthetic route to Pechmann dyes. This one-pot reaction affords three donor–acceptor–donor quadrupolar molecules (P 55 -1, P 66 -1, and P 56 -1); P 56 ...


Blue-Emitting Butterfly-Shaped 1,3,5,9-Tetraarylpyrenes: Synthesis, Crystal Structures, and Photophysical Properties

Nobuyuki Seto, Takehiko Yamato, Xing Feng, Jian-Yong Hu, Fumitaka Iwanaga, Mark R. J. Elsegood, Carl Redshaw
Org. Lett. | 2013 | 10.1021/ol4002653

The first example of aryl-functionalized, butterfly-shaped, highly fluorescent and stable blue-emitting monomers, namely, 7-tert-butyl-1,3,5,9-tetrakis(p-R-phenyl)pyrenes, were synthesized by the Suzuki–Miyaura cross-coupling reaction from a novel bromide...


Reversible Synthesis and Characterization of Dynamic Imino Analogues of Trimethine and Pentamethine Cyanine Dyes

Kamel Meguellati, Martin Spichty, Sylvain Ladame
Org. Lett. | 2009 | 10.1021/ol802913b

A new family of unsymmetrical imine-based trimethine and pentamethine cyanine dye analogues is reported that can form under reversible and thermodynamically controlled conditions from non- or weakly emissive amine and aldehyde building blocks. These dynamic...


Fluorescence Photoactivation by Ligand Exchange around the Boron Center of a BODIPY Chromophore

Erhan Deniz, Burjor Captain, Subramani Swaminathan, Sherif Shaban Ragab, Françisco M. Raymo
Org. Lett. | 2013 | 10.1021/ol401380n

Chelation of the boron center of the borondipyrromethene (BODIPY) platform by a catecholate ligand results in effective fluorescence suppression. Electron transfer from the chelating unit to the adjacent chromophore upon excitation is responsible for...


Syntheses and Tunable Emission Properties of 2-Alkynyl Azulenes

Koushik Venkatesan, Michael Koch, Olivier Blacque
Org. Lett. | 2012 | 10.1021/ol300327b

Various substituted 2-azulenes have been synthesized via Sonogashira coupling. Doping with superacids allows tunable emission from 443 to 750 nm depending on the substitution. The proton doped compounds are the first azulene alkyne based systems that show...


Steric Strain Release-Directed Regioselective Functionalization of meso-Methyl Bodipy Dyes

Subrata Chattopadhyay, Neelam Shivran, Tapan K. Ghanty, Soumyaditya Mula
Org. Lett. | 2011 | 10.1021/ol202490p

Starting from some meso-methyl Bodipy dyes, the corresponding meso-styryl derivatives were synthesized by regioselective Knoevenagel-type condensation with different aromatic aldehydes. The reactions were driven by the alleviation of the structural strain of...


Universal Dark Quencher Based on “Clicked” Spectrally Distinct Azo Dyes

Pierre-Yves Renard, Arnaud Chevalier, Julie Hardouin, Anthony Romieu
Org. Lett. | 2013 | 10.1021/ol402972y

The first synthesis of an heterotrifunctional molecular scaffold derived from the popular DABCYL azo dye quencher has been achieved. The sequential derviatization of this trivalent azobenzene derivative with two other nonfluorescent azo dyes (Black Hole...


Synthesis and Properties of a Covalently Linked Angular Perylene Imide Dimer

Karl J. Thorley, Frank Würthner
Org. Lett. | 2012 | 10.1021/ol3029115

Utilizing the unexplored chemistry of a monocarbon analog to perylene bisimide, a covalently linked angular perylene dimer was synthesized. On the basis of measured optical properties and molecular modeling, the spectral changes relative to a monomeric...

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