Content 1 Intoduction 2 Types of NIR Dyes 3 Experiment procedure 4 Application 5 Literature 6 Reference

1. NIR DyesNear Infrared Dyes
M.Sc Chemistry
Progressive Presentation on

2. Content
 Introduction
 Applications
 Experiment Procedure
 Literature
 Reference

3. Intoduction
NIR (Near Infrared) Dyes are High quality reactive and non-
reactive fluorescent dyes ranging from blue to near-infrared,
as well as dyes with an exceptional large stokes shift which are
ideally suited for multicolour labelling and fluorescence
microscopy or flow cytometry applications.

4. Types of NIR Dyes
 Phthalocyanine and Naphthalocyanine dyes- It is well known that
phthalocyanine chromophores were first designed and synthesized as
NIR absorbing dyes in 1928. After this introduction, phthalocyanine
chromophores were structurally determined and recognized amongst
the very important dye and pigment classes, especially those
chromophores which showed the colour blue.

5.  Polymethine dyes- Methine dyes have been used for some time and
cover a large wavelength region. In other words, polymethine dyes
show the well-known structure and their absorption ranges cover a
wide range of wavelengths from 400 to 1300 nm.
 Quinone dyes- Dyes containing the quinone chromophore have
recently been used effectively in the dye colorant industry. Quinones
are generally used as electron acceptors in dye design and synthesis.
Donor and acceptor introduction into the quinone molecules causes
wavelengths to change from a visible adsorption to an infrared one
with an intramolecular charge-transfer (ICT) system.

6.  Azo dyes- Azo dyes are one of the most widely used chromophores
in dye chemistry. In general, however, they absorb in the visible
wavelength region and are not suitable for NIR absorbing dyes.This
type of dye is used in many different dye classes in the textile dyeing
industry and generally absorbs between 350 and 650 nm.

7. Applications of NIR Dyes
 Laser optical recordings- As the name implies, optical data recording
[1,2,3,4,5] or optical data storage is a technique for storing and retrieving
data using optical property applications. [6,7] Disks or tapes were widely
used for most data storage but in order to increase the amount of data
per unit area, a new type of recording method using optical properties was
developed.

8.  Laser printings- A semiconductor diode laser is currently used in laser
printers as the light source. It emits NIR light at around 800 nm
wavelengths. To respond to this NIR light, photoconductive materials
sensitive to an NIR wavelength such as infrared absorbing dyes are used
as photo-receivers.
 Biological/medical applications
i. Bio-Imaging- Fluorescent dyes based on small organic molecules that
function in the near infra red (NIR) region are of great current interest in
chemical biology. They allow for imaging with minimal auto
fluorescence from biological samples, reduced light scattering and high
tissue penetration. Here in, examples of ongoing NIR fluorophore
design strategies as well as their properties and anticipated applications
relevant to the bioimaging are presented.[8]

9. ii. Cancer Targeting and Imaging- The overall objective of this study is to non-
invasively image and assess Tumor targeting and retention of directly
labelled.[9]

10. Synthesis of TCH (Thiocarbahydrazide)
Take CS2 +
Hydrazine
Hydrate
Heat for 3-4 hours
Filter
Washing with
Ethanol and
Ether
Recrystallization
with dil. HCl

11. Synthesis of NIR-1
Aldehyde + TCH +
Ethanol
Heat 3-4 hours
Filter

12. Structure of TCH, Aldehyde and NIR-1
N C l
C H O
2 - c h l o r o q u i n o l i n e - 3 - c a r b a l d e h y d e
C
H N
S
N H
N H 2 N H 2
t h i o c a r b o n o h y d r a z i d e
N
H
C
N
H
N
C S
N H
N
C H
N
( 1 E ) - 1 - ( ( i s o q u i n o l i n - 3 - y l ) m e t h y l e n e ) - 5 - ( ( i s o q u i n o l i n - 4 - y l ) m e t h y l e n e ) t h i o c a r b o n o h y d r a z i d e

13. Literature
 In Near-infrared(NIR) absorbing
dyes Near infrared dyes show light
absorption in the near infrared area of
700-2000 nm. Their intense absorption
normally originates from a charge
transfer of an organic dye or metal
complex. Materials of near infrared
absorption involve cyanine dyes
having an extended polymethine,
phthalocyanine dyes with a metal
center of aluminum or zinc,
naphthalocyanine dyes, nickel
dithiolene complexes with a square-
planar geometry, squarylium dyes,
quinone analogues, diimonium
compounds and azo
derivatives.[10,11,12]
Reference
1) Science Direct (sciencedirect.com)
2) Wikipedia.
3) Books -
i. Jones,F.Reu.Prog. Color.Relut. Top.
1989,19,20.
ii. Griffiths, J. J. SOC. Dyers Colour. 1988,
104, 416.
iii. Yoshida, Z., Kitao, T., Eds.Chemistry of
Functional Dyes; Mita Prese: Tokyo,
1989.

14. Reference
1. Matsuoka M (1990), Infrared Absorbing Dyes , Plenum Press, New York.
2. Fabian J, Nakazumi H and Matsuoka M (1992), Near-infrared absorbing dyes,
Chemical Reviews , 92 , 1197–1226.
3. Gregory P (1991), High-Technology Applications of Organic Colorants , Plenum Press,
New York.
4. Peters A T and Freeman H S (1994), Modern Colorants : Synthesis and Structure
,Kluwer Academic Publishers, London.
5. Kubo Y, Mori F and Yosida K (1987), Syntheses and characteristics of naphthoquinone
methide near infrared dyes for optical storage media, Chemistry Letters ,16, 1761–1762.
6. Chen D I and Zook J D (1975), An overview of optical data storage technology,
Proceedings of the IEEE , 63 , 1207–1230.
7. Bartolini R A, Weakliem H A and Williams B F (1976), Review and analysis of optical
recording media, Optical Engineering , 15 , 99–108.
8. Escobedo, Jorge O.; Rusin, Oleksandr; Lim, Soojin; and Strongin, Robert M., "NIR Dyes
for Bioimaging Applications" (2010). Chemistry Faculty Publications and Presentations.
56.

15. 9. Fatma M. Youniss, Gobalakrishnan Sundaresan, Laura J. Graham, Li Wang, Collin
R. Berry, Gajanan K. Dewkar, Purnima Jose, Harry D. Bear Jamal Zweit October
21, 2014
10. Jones,F.Reu.Prog. Color.Relut. Top. 1989,19,20.
11. Griffiths, J. J. SOC. Dyers Colour. 1988, 104, 416.
12. Yoshida, Z., Kitao, T., Eds.Chemistry of Functional Dyes; Mita Prese: Tokyo, 1989.