Some images not loading to mobile devices.

So I'm having issues copying  few images form iPhoto on my iMac (Mountain Lion) to both of my mobile devices.
These images used to be on both of my devices but for some reason have now disappeared from them and refuse to copy back to either my iPhone and iPad.
I initially thought these images may have got corrupted somehow so I deleted them from iPhoto and replaced them with new copies. All of the files are in jpeg format and smaller than other files i have in iPhoto which copy to my mobile devices successfully. This had no effect which I find a little strange.
I then tried the following, none of which has worked;
1.     deleted my iPod photo cache
2.     rebuild iPoto Library (each box was ticked and the repair/rebuild undertaken before closing iPhoto and moving on the the next repair/rebuild action)
3.     Number 2 didn't work so I deleted my iPod cache again.
4.     Disk utility  - verify & repair permissions
I still think that it may be corrupt file issue as all of the images used to successfully copy to my devices in the past without issue.
But if this was the case, surly when these images were deleted and replaced with new jpeg images (made from my master PSD of TIFF files via photoshop) they should then copy over successfully?
confused.com

As a Test:
Hold down the option (or alt) key and launch iPhoto. From the resulting menu select 'Create Library'
Import a few pics into this new, blank library. Is the Problem repeated there?
Post back with the result.

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